Yes, playing a none human should be harder and everyone shouldn't be on the exact same level. However potential IC reasons are lacking from your point. You only pointed out that OOCly it should be hard for them for the sake of it being hard, regardless if there is logical IC reasons as to why something was done.
Removing a few trees for easily get about makes logical sense for outcasts, specially when all that stands in your way are only 3-5 smallish trees. All of which probably easily cut down in a single night. Specially if its via someone of immense strength, such as a brute caliban. Allowing them to circumvent the main road, which makes no sense for them to even try traveling at day, and is still risky at night when there will likely be predators out.
Looking from a OOC perspective, this is the starting area we are talking about. Where you have absolutely zero choice in where you start, even if your a local. it is fair to label that lack of choice as apart of the challenge. Even if the point of outcast and caliban chars is to roleplay out struggle, there is still endless amounts of such given they cant enter the city, interact with npc, have various services denied to them that others can use. Making the initial starting area easier to reach the well wont cripple the level of struggle and challenge for caliban/outcasts. Specially when a perfectly logical reason can be given as to how it came to be. No one is asking for the well to be immediately attached to the well or asking for unrealistic changes.