Lots of great advice. Especially the advice, that includes getting to know the property as much as possible. I've said this many times, but don't be afraid to walk around. It's a great idea to id early season rubs(likely buck bedding!) where rubs show up during the rut(buck travel corridors/ doe bedding) scrape lines! Random scrapes!
Of course trails!
It's your call on ending crp contest. Being a $ decision.
Also where neighbors are hunting=important
You need to get to know the property, no so called professional could ever give this! You are already listening to the old property owner-that's really really smart!
Than u can set food plots up after you start figuring things out. I know the so called pros always call for using the border to access stands. That might work in some places, but your topography and and woodlots put u walking right through your bedding. Especially if the neighbors don't hunt.
All this info you will learn is something Steve or anyone could ever give u. Take that $500 and buy that many more trail cams. Info gathering!!!!
Did I say, At this point it's all info gathering. Sure u will bump deer and maybe a big buck. Well that's all info gathering and if u are in it for the long hall, that short term sacrifice is worth the long term knowledge. Anyone can draw on a map saying a deer will bed here or there, but deer a simple animals.
I know this offends some guys, but I'm a hunter! Maybe it's my ego too, but I'm gonna be patient and learn things. It's fun and challenging to learn a property. Sometimes it's easy. Deer aren't some phantom ghost, they are really dumb animals that go off instinct. Some people want instant satisfaction but a guy like Steve could never determine some of the things I mentioned by looking at a map! He can make general inferences but you'll be able to do that after a few sits. I don't care how good of a whisperer many think he is!
You seem like a pretty sharp hunter, just stick with the basics and learn!