I am actually in a simular situation. All of my normal gun season spots are being leased or sold off here in IL. But I have access to my inlaws 100 acres of woodland in southern Indiana where I am the only person who hunts it. I believe the $295 I paid for the tags this year will be worth it for the following reasons. 1) I still fill my freezer full of meat. 2) I treat it as vacation and really enjoy my time. 3) I see my family while I am there and since they are 4 hours away we don't see them that often so its nice to catch up.
It all comes down to do you have the money to spend and do you want to spend the money. Luckily for me my wife knows I need my time in the woods!
Good luck with either choice you make