A neighboring property, similar to my current rental property, is now on the market at the same price I paid two years ago, with comparable rent.

It puts this property considerably above the top of the market, would that really make sense for a rental property? 

You would buy there to live or if you just want to own property in the best location possible....Overall, the long term rental game is rather difficult in the middle TN market right now, especially in the Nashville area.

I am not sure how the owner occupancy requirement of the JADU impacts value, but is will impact value as there are many RE investors who do not want to owner occupy.You should be able to determine the value by calculating NOI and knowing the market cap rate.  

They may be able to transfer title to LLC after closing, but it will be best to check with your lender if there are any restrictions to do so prior to that lender selling that loan in the secondary market. 

Unfortunately, certain markets are much more difficult to evict than others.Going forward, I would try to set clear expectations with your residents, and when they violate one, they need to be held to account. 

It is a very competitive market here with restrictions all over the place. 

From my internet sleuthing I knew the owners were in at least their late seventies, lived all the way in Oregon and had owned it for nearly forty years.

I own a few properties throughout the Chicago suburbs and I'm looking for a new market.

Do they need some "sprucing up" ($2-3k) to get market rents or do they need more extensive renovation. ($10+k)- How is the building appear from the outside?