@Edward Mahoney  You're correct that FHA is owner occupied and as memory serves me, it's supposed to be at least 12 months unless there's some verifiable reason like a job transfer.Don't fake the owner occupancy bit. 

In addition to the above, once you put your apartment online for rent...you will know if it's reasonable or not based on the number of inquiries you receive.I just placed my 1/1 w/ Office online and received 60+ inquiries within 2 weeks.

If you are doing one or two flips a year, maybe not - although for asset protection reasons it would be better to make them in LLCs (plus there are other tax considerations).

This doesn't mean you shouldn't offer but have reasonable expectations on chance of acceptance, my gut puts your odds of getting the property at 10-15%

- Is there any reason this may be a bad idea or anything I'm not thinking of? 

I agree with others that he is trying to hide something, and hoping you'll overlook the background checks by figuratively waving a fistful of cash in your face.Many good reasons mentioned above to avoid a tenant that wants to prepay all the rent. 

Neighborhood is about b to b- in wisconson.1 of the applicant mentioned they want a better neighborhood as for reason for moving.

Most rental insurance policies have a liability portion for that very reason, if you are found negligent. 

First you have to decide what your reason for investing is So, Decide which kind of investor you want to be (SFR, Commercial, Land, Tax Liens, Passive, HML, Multi-Family, Notes, Fix & Flip, Buy & Hold, "Subject To", apartments, duplexes, assisted living, REOs, Foreclosures, Short Sales), etc.

A house in which multiple consumers from all walks of life could see themselves there and the cost is reasonable to them, can easily slip into a bidding war.