I think part of the breakdown here was the usage of "tresspass".

I'm using it in the general sense of an individual illegally being in a location they would otherwise be legally able to occupy.

My old friend from high school is prevented by his probation to enter places that solely have a liquor license.

He's not actually trespassed from each location individually, but is defacto trespassed from all.

You're right, in most situations there are more relevant charges, and "tresspass" as a charge likely will not be levied, there are better options.

I'm sorry if i was crass, this subject is upsetting to me. I have exhausted myself trying to explain some of this to various public agencies, in addition to explaining to coworkers their client has very little chance.

Easements are a pretty sore subject.