RE: Should I use an outfitter? (PLEASE READ)
Save your money ... and instead of waiting till hunting season starts to hit the WMA down the street, cruise around in the spring and summer asking for permission from everyone you meet, even offering to do some chores or help out somehow. Ask local farmers, and check local plot books for owners of large private owned land and make phone calls.
If you did all these things I promise you would soon have more land to hunt than you could cover in a season and at least some of it won't be covered in orange. You may even bump into some other hunters who put in the same kind of effort you did and they may offer to help you out with some pointers or tips. May even meet a hunting buddy.
Like anything .. put in the effort and you'll find the land. You'll be told no a bunch of times, but even they sometimes direct you to people who say yes.
Of course if you don't want to put in the effort, and it does require effort, you can always pay someone to take you out and point you to where the deer are. What ever works for you.