The original cabinetry was an outdated maple door style.

These are desirable areas where you would actually want to buy a house to flip or hold as rental because they have good schools, safe neighborhoods and  little to no "war zone" type streets.I drove EACH street looking for houses that are either outdated or needing serious repairs (based on exterior appearance).

Become a live in flipper, you buy your first home a fixer upper (out dated ugly, but still good for an FHA loan), fix it while you live in it for about 2 to 3 years, now you have increased the equity/value, sell it cash out the equity get your next fixer upper put down only the minimum for the down payment,  live in it for 2 or 3 years fixing it as you go and repeat, you are now making your "snowball" of money bigger.

Perhaps you could let him know that you will set an expected move out date and in the interim you will show the property to prospective tenants.  

The banks here are little outdated in terms of technology but the service is good.I have accounts at BofA, Chase, and Wells Fargo and still use them regularly solely online.

Prior to him I had a older CPA that was outdated.  

The house is in a decent (c+) neighborhood, and is quite outdated inside as far as styling.

I've looked around and found some but they seem to be outdated or not current listing.

I'm considering a rental agreement that states the move-out date in the contract (with option to extend under certain terms), and has them pay the full 2-3 months' rent up front, with a half-month security deposit also due prior to taking residence.

Options are not easy anymore, they can be done safely and with profit motives, but you'll not be getting all the current stipulations from other investors or gurus using outdated tactics, to the contrary, your deal can blow up relying on old tactics.Caution again, you cannot require a buyer (optionee) to perform any obligation in an option contract, tying performance under a lease to the option certainly becomes an installment sale.