However, realistically.....most buyers are going to wait until after school lets out in most areas before they start looking to move so they don't risk moving their kids from their current school district. 

The entire town is in a property owner association(basically and HOA).

Basically, you are trying to jump the gun.

While all of this may seem obvious, I have personally encountered all of it in flips in my market, so clearly not every flipper thinks about something as basic as "can my refrigerator door open all the way?".

Basically appreciation potential, and potential cash flow follows all that.  

The basic fees on a loan make up too high a percentage on low priced loans which classifies them as predatory.

I e-mailed the city council people and the response I got was basically "We're not allowing more than 250 STR's in our city so get in line".

Expense ratios vary dramatically depending on project size, age and other factors, but basic rule of thumb is the smaller the project the higher the expense ratio's, using a 33% expense ratio for a small facility (less than 150 units) is optimistic, smaller facilities are probably closer to 40%.

Basically I get one month of additional rent for my troubles, and the rent is paid in full throughout (either by them or the new tenant)Am I letting them off too easy?

There are a lot of assets in Columbus that are basically turn key properties, and even if you have some minor renovations (5k-10K)I would recommend trying to go after an interest-free credit card AFTER you are approved and close for your loan.