Yup it is always a catch 22 situation. The way land is being gobbled up and posted I don't know if it is worth waiting for the ax to fall. On thing for sure things will change over time. It always does and usually not to our liking. Some landowners just don't want to be bothered with all the details and don't want to be the center of any controversy. I guess I too would sit tight and closely watch what is happening. I think you are absolutely doing the right thing by plowing him out and helping with storm cleanup. The more effort you make along those lines the better standing you will be in to keep it as it is. As time goes on and some guy with a ton of bucks comes up to him and looks to lock himself in and you out the landowner might just tell him that he keeps his land open to a few friends and he isn't interested in ending that. All this works if he isn't hurting for cash and you need to judge all of that. I live in Vt and the state has always been an open hunting state, meaning that if any property wasn't posted then you could legally hunt it unlessthe ownerverbally told you to leave. A couple of years ago the state decided that anyone who put up a tree stand, either a permanent or even a temporary hang on, needed permission from the landowner to hunt. Many landowners knew people were hunting on their land but didn't mind unless there was a problem. When asked for permission it was too easy for lots of them to just say no. I am still able to hunt on most of my spots but I think that law did result in some land to be off limits. If you do decide to make an offer to the guy then I would hope you would talk with the other couple of guys who also enjoy the spot. I would hate to be them and get shut out.