Most often when someone crosses a Property Line to hunt they know they are doing illegally. There are certain times when they don't.
I knew and hunted with a guy that offered to take me along with him to a nice spot next to a buddy's of his house. He had been seeing some nice deer from the house and sometimes even in his yard. The Buddy said he knew who owned it and it was OK to hunt there.
After a couple of times being there the Guy I knew started feeling weird about it and asked me if I wanted to go along with him, which I did. It didn't take me long to figure out this was a nice Property and wondered why the Owner allowed anyone to hunt there. Then I did a Property Appraisers website search and found who actually owned it. After I knew I asked the "friend" that gave us permission to hunt there Who Owned It and he had No Idea.
That was it for me. We did eventually find the Guy who lived on the Property and he was NOT able to give us permission to hunt there, he couldn't himself. Seems the owners were keeping it as an Animal Sanctuary and he had got the Rights to have Cattle on it but no Hunting was allowed.
BTW in the state of Florida Trespassing with a Firearm is a Felony with an Either Or OR Both of 5 Years in Prison AND/OR $5000.00.
I never went back. I even left a new Hand On Stand in there that I had put in a Big Oak Grove that I was able to climb up into by just using the splits and branches.