Finally, check with the Town to make sure there are no municipal liens, Make sure they're on Town sewer, check with the tax assessor to see how many bedrooms the tax office thinks there are, (important if you are flipping) buy ok to have more bedrooms if you are planning to buy and hold.  

I am drafting the lease and planning to take it with me to closing, where we will be executing the document.

Legitimate, in this case, means that the entity is part of an overall business investment strategy whereby you have a business plan, tax returns, and the funds you seek are for further business expansion.If, however, the LLC is a stand alone entity, is not profitable, or is not legitimate, then your probably better off putting into your personal name and securing funding that way, or still talking to local or regional banks to see if they have any loan programs available where you might be able to secure financing.

I’m planning to purchase some land and build a small 12x12 cabin.

Do you plan to live there forever?

I am planning to get into the TN real estate market as my first investment and am looking for some information.In particular: Areas to steer clear of, property management fees, typical cosmetic rehab costs, etc.My strategy is to put large down payments on 2 properties (relative to housing prices) to help pay for my living in NY while still gaining appreciation in a growing real estate market.

If you do a furnished LTR you will still have to worry about your furnishings and possibly consumables/linens if you plan on providing that sort of thing. 

Let me know if you plan to make it so I can let the owner know and he can make sure they are properly prepared.

Chances are, they will avoid you because they are not planning to report this income.

Set action plans that your going to strive for ____ and if by __ date plan A fails, you roll too plan B.