I do not know anyone in Tennessee, and I am planning on building connections there and getting to know like minded individuals.

Unmarried individuals can exclude up to $250,000 in profit from the sale of their main home or $500,000 if you're married.

It all depends on the individual.

I have a SFR and I am planning to rent the rooms out individually.

So every deal is unique, your goal is to have relationships in each of these buckets, stay in contact, and underwrite each deal individually.

I recommend setting up keyword alerts for each area as they are discussed in the forums daily with advertisements posted in the BiggerPockets marketplace hourly.One thing to note when looking at the individual markets, you can make or lose money in any market.

The lender is a local private individual who has helped finance several deals for me over the years.

Please reach out I would like to connect you with like minded individuals in ChicagoLand  >> https://bit.ly/JimBiggs

I have been planning on 1031ing up both my LLCs at a later point (individually because one is a partnership). 

You are probably going to need to do individual property analysis, I don't think there's a good rule of thumb here.6.