Something I've noticed a lot in this so far have been a great deal of punitive measures taken to enforce the setting - to make the night more dangerous, to punish certain behaviours and such like. I also saw an incentive to empower evil roleplay - I fear I disagree with that, as its fundamentally unfair and extremely prone to exploitation, but it 'did' bring up an idea of trying to find a way that doesn't punish behaviour, but instead encourages certain types of behaviour instead.
How do we do this? I'm not sure. I do however know a few downsides to punishing over rewarding. We've got a lot of new characters, a lot of new players. Some aspects of server culture have changed over time or been discarded, and some others have been forgotten. A lot of people however don't know the secrets, tricks and knacks and a fair few struggle to get moving along.
A lot of the changes proposed would punish these people starting out. When one speaks from a position of experience, its easy enough to forget the trouble those without that experience can have. It can be dissuading and for a lot of folks either just starting out, or even starting a new character, getting thoroughly stomped on for not knowing the ins and outs of the place does nothing to encourage people to keep playing. Sometimes it doesn't take very much at all.
Punishment can do little except create an alienated, adverse reaction, especially when the individual being admonished isn't quite sure what they did except 'be out at night'. As it stands it can be plenty scary enough as it is! But just because its no longer scary at level 10 or higher doesn't mean the level 2 isn't still being punished by what you can now survive. You have to keep the little guy in mind, like you'd have wanted for yourself at that time.
So, instead, on top of Cassius's and Erebus's suggestions, I have a few more ideas, some of them outside the box, for the purpose of encouraging player driven roleplay, that revolve around the concept of rewarding rather than punishing.
1. Tagging Tool.
This one I'm not so sure how to implement, but it would be using a tool on the hotbar to tag another player. When tagged, there would be a range of options to come up, that would then flag in the DM channel. The flag would then have a description on it like so - 'Player A has tagged Player B for Atmospheric Roleplay' or 'Good PvP conduct' or something along those lines. The DM would have to observe the behaviour, and oversee it. If they don't see anything or enough to warrant further, they can then ignore it. The tag itself would have a cooldown of 60 real life minutes, to prevent spamming. But if it brings to the attention of a DM who may or may not be watching (as always, there will be no direct indication of DM presence) then the DM in question may reward the tagged player.
This does not leave rewarding in the hands of the player. Its purely in the hands of the DM watching, and the reward given may be either xp or some other manner of reward that is at the DM's discretion - even a bit of NPC interaction might well be all that is needed. But it is an ever present incentive to players to play at their best, to improve themselves, to push their roleplay harder for the notion of a reward that they know to exist. As it remains in DM hands and the DM's have shown themselves to be highly discretionary, it remains out of the reach of exploitation, but it 'does' give some perhaps unsung stars a chance to shine.
2. Expanding Factions.
This isn't meant as a disrespect to our current factions - I have a lot of love for them, but I also think we need to expand on a few things to give players some new or seldom used options that can offer new incentives in roleplay. I also recommend it for the fact our player base is much larger than it was only a short while ago, and as it is larger there are far more openings for different factions. This part here is probably one of the biggest ones in terms of work required and I'm well aware of that - but it once established much of it is self governing, and interfactional conflict is often its own reward. Now, this does create issues in that faction conflict may or may not be something outright desired by the team, but if it is an option, then there are quite a few things we can look at. Some ideas for factions, and what they would require, I'll list below -
-Red Wizards of Hazlan.
This one is honestly pretty much already done. The work on this faction has been consistent and lengthy and they deserve to be recognised as an official faction at this point. Best of all they probably require the least amount of Dev work to be established. They have their base, they have all they need to function already in place. It might as well be legitimate.
-Lawgivers of Hazlan.
Not too sure how much more work this would require, but its a group that could rise up with the Red Wizards, working in both collusion and conflict with them, much like most of the other factions. Truth be told most factions do not function unless they have something to bounce off of, in concert or conflict.
-Rebels of Hazlan.
This one is work intensive. It would need a base of operations, codification of its membership and roles. Possible thoughts would be a 'underground railroad' for the purpose of finding and rescuing non human slaves, getting them out of Hazlan or teaching them to fight back themselves. It would be a struggle and in a very difficult position, but it would give players opposed to the Red Wizards a base of operation, and something for the Red Wizards and the Lawgivers to strive against directly, adding an element of danger to each of the factions if either one becomes good at what they do.
-Wardens of Barovia.
This faction would exist for the purpose of being direct agents of the Count - either for Strahd himself or those who exist below him. Human agents who fulfil his will, hunting down existing bounties that might exist outside of Vallaki (if they warrant interest). This faction would operate in any and all of the areas of Barovia, and be a danger to those that think they are out of reach of punishment.
-Degannwy, Dvergheim.
These factions probably are much like the Red Wizards faction, in that making them official and supported is somewhat overdue. Giving them a codified, solid position as factions would work by giving them roles and responsibilities; the dwarves could do with a formal ranking system due to their lawful nature, that could create leaders and workers amongst them. Elves, being more chaotic, would fit roles suitable to their classes - arcanists, nature protectors, soldiers, etc. By giving them something more formal they can create amongst themselves a set of faction orientated goals. This would require little Dev work overall - most of what they need already exists, and frankly they can already function. A bit more formality to it would give each faction structure.
-Gundarak Rebels.
I truly want to see this one happen, but the circumstances of it happening are extremely work intensive, and thus it is moved more into the 'wish' territory of things. The only way I see this faction working properly is if it has a place to set itself that the work of Vallaki garda cannot get to it, at least not in any way easily. The logical place to put it is where the main source of them comes from in the lore - in Zeidenburg. In order to do that, the city needs to be added in game, and it is, by lore, a very large place indeed. This would change the fabric of the landscape of Barovia considerably, maybe too much. But it would also give intercity/interfactional conflict a possibility while also providing what the Red Wizards proved so incredibly important to their creation and stability, a relatively safe base of operations for them to stage out of. But the dev work required is huge, a city with dungeons also attached is no small order, not by a long shot.
-Alanik Ray's Detective Agency.
This one is a little out there. But I would like to see a good aligned investigative faction in Port, a sort of partnership to the Wayfarers, but operating independently from them, in a rather more international sense. It does not of course need to be Alanik's, but could in fact be a result of player and DM partnered driven initiative. But a rather more openly good aligned faction in Port (like how the Wayfarers and Morninglordians are in Barovia) could be an interesting balance against the suggested evil factions listed above.
-The Kargat.
This one is out there, and very much a difficult one, but its one that I also really like the idea of. Monsters, working as part of Azalin's secret police, operating in various locales of the server, gathering information, acquiring knowledge and acting as spies, disruptors, and adversaries for the server at large. Weeded out by the application process to prevent them becoming too much of a problem, players can be recruited into their number as MPC's. This one would need some oversight, and would need a lair as well that they can use - them and them alone. I'd probably suggest a travel NPC that only they can use that can take them to where they need to go. But a perpetual monster faction 'could' prove exciting. They come into existence in a small number and for the achieving of objectives in their six month period, before fading out once more. It would not of course -have- to be the only choice for AMPC's and such, but giving them a stable base to set out from gives them a grounding of objectives and factional basis that allows for a self perpetuating story that the server can only grow from.
I understand most of these ideas are just that, ideas. They require work in all aspects of the server - a more codified lore, dev work, DM attention, and more. By absolutely no means would I expect to see all of them implemented, I'd be happy to see even two of them make it in, but I listed the suggestions to give some ideas of what could be the most interesting, the most fun, and the best at giving players something new to work with that they haven't yet experienced before.
3. A new, expansive and helpful write up of the server, for the purpose of expectation management.
This one is sort of self explanatory, but only sort of. I believe what would be very helpful for players is a single thread that covers everything currently in the FAQ, but also some new, helpful suggestions for people, and a mission statement of expectations from the DM's to the Players in terms of what they hope, but not demand, that the players do. Examples being:
The correct circumstances that warrant a server reset.
The sort of thing a player should and should not put in their player description.
Realistic expectations of playing a certain alignment on the server.
Realistic expectations of playing an AMPC or MPC on the server.
Encouragement of atmospheric roleplay, and the importance of respecting the setting.
Why and how closure is encouraged.
How DM's would prefer to be interacted with by the player base.
How the player base should treat one another, both directly and indirectly.
How the passing of time works, how real world and in game languages work,
etc.
A sort of guide that goes beyond the mechanical to the server, and more of an explanation of some realistic expectations of the player base. A lot of this stuff is probably obvious to folks on the team, but that doesn't mean that its obvious to the player base at times, especially new players who are not sure where to look or find this sort of thing, or worse, are basing their behaviour or methods in these fields and others because of erroneous information passed down second hand or from other server practices. Clarity is always a good thing, while maintaining the necessary levels of opaque information that is required for the server as well. Gathering this information however, can both clear things up for a players on an ooc level while gently promoting certain things, behaviour, and methods of roleplay in character, which in turn would foster self driving roleplay.
I might add to this whole thing, and it may well get torn to bits, but this is purely just idea spam. Hope it helps.