Great idea's. Here is what has worked for me.
I go in the spring, usually around April, May. I provide a writting form with all my information, Vehicle, phone number, Hunting Liscense. State of WV requires you have written permission and it must be carried with you when you are on their property. So I have a form that just adds extra info. The landowner keeps one and I get a copy.
I ask in spring if I could hunt Ground hogs with my bow. Usually they laugh about that, but then say sure go ahead. Then when I go out there to go for ground hogs, if I see the farmer working on something or even not. I always first offer up to give them a hand. Then usually around august, I don't even have to ask for permission for deer. 8 out 10 times, they come to me and ask if I would like to also like to hunt deer. The one big issue I have heard from every farmer I have spoken with is that they hate when folks show up just a couple weeks or even days before season opens and ask for permission to hunt, but do not want to give anything in return and then are upset when the farmer says not this year. I always try to put myself in the landowners shoes and ask myself. If this were my place how would I feel and what would I expect.