One option most ponder over is becoming a Real Estate Agent in the desired market area and is even advocated for in the BP Podcast.The main reason a License is beneficial seems to be due to the ability to be your own buyers agent and save on some closing costs as well as a foundation on which to understand the paperwork and processes of a standard transaction. 

Hi, I just recently got my Tennessee real estate broker's license and primarily do business in Georgia & South Carolina where the GA & SC Association of Realtors provides members a ton of standard pre-printed contracts, including a Residential Property Management Agreement that is to be signed by the homeowner and broker.

We urge you to think long and hard before you deviate from the standard and time tested way of charging and accepting rent monthly.

I did have issues with this service.Another one is http://flatfee99mls.com/   $99 one time fee.The buying broker produces the offer to purchase.You can find standard purchase and sales agreements on line. 

The cash out refi & the purchase mortgage could be standard conventional mortgage for both properties, If you have more questions feel free to DM me 

If you only have 1 property, then a standard LLC would probably work for you and is much cheaper to setup in Indiana than a Series LLC.

The VA loan offers a great incentive that you don't have to put money down, and you don't have to pay the PMI for having less than the 20% down payment... but know that their standard VA loan fee, based on a percentage is a higher percentage than your first VA loan was.

Standard terms on smaller deals are 5 year fixed rate, and a 20 year amortization.  

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