Its a 4 unit, so I suppose I'll be looking at comps all day to see how it sizes up. 

The track season short term rentals and constant demand from people employed at the Navy training facility could make it work well for buy & hold. 

When you're self employed it's WAY more difficult to get a loan approved and I think you have to prove income as being self employed for 2 years.

We are a small to mid-size town of 300,000 (600,000 metro region), situated between Columbus, Detroit, Cleveland, and Chicago.

When you are self-employed, they are irrelevant.

Generally , these homes should be close in location, layout, size, age, and condition.

Also something I didn't mention is there is a generous sized fenced in back yard with a garage.

Verify their income and employment .

Tax strategies can certainly boost returns, regardless of what real estate strategy you employ, but I think asking "do the higher short-term returns make up for the tax consequences" is somewhat backwards. 

When building spec homes, how do you determine the size of homes to build?