We can't buy with a traditional loan for another 7 months because my boyfriend's job switched from 1099 to W2 the year before last.

A lot of traditional analytical templates, p&l sheets I found online don't really factor in some of the unique nuances of short term rentals like this.  

This has the potential of being a 12 month rental, but not in a traditional vacation rent way. i have been told that a lot of the local and seasonal vacation employees  need places in the off season.  

If you are looking to buy a rental, you'd want a more traditional type mortgage.

Sevierville cabins are more traditionally "out of the way" and quieter (at present).

But if it is a traditional IRA, both gains and contributions will be taxable and early withdrawal penalty will apply when you take it out before you reach 59 1/2 years old.

Southern IL has a lot of markets where more traditional housing competes with the affordable model, which is not ideal.Next, anyone looking to help you out here will need a tad more information to assist you in an evaluation.  

The property is an older home, built in 1880, which needs some finishing -- so it might not meet all the requirements for a traditional mortgage loan.

I am aware of some of the general financial indicators analysts use when making a decision about a deal, but, are there any others investors like or would like to see on a CMA that aren't traditionally thought of?

He mentioned that he was more interested in a traditional sale and after speaking for about 20 minutes we left off with me wishing him luck on his sale and him saying that he will keep my offer in mind.