We don't pay vendors by credit card or cashapp because it is far too hard to keep the accounting straight with a high volume of transactions to do that. 

As already mentioned, you could sell via seller financing to lower AGI, as all you would have to claim is the payment income - until balloon payment received.Did know an investor that had 14 properties paid off and he moved into one every two years to then sell with the $250k single exemption.

I have some of the required funds in a HYSA, but will most likely need to draw from another account and I'm curious which method is the most efficient in terms of taxes/capital gains, penalties, loan repayments, etc.Based on my previous transactions in the market, I estimate ~$45k cash to close: $20k for the down payment, $15k for closing costs and prepaids, and $10k of starting reserves.

Umbrella insurance provides substantial liability protection at a lower cost and avoids the administrative complexities of managing an LLC.

I has two GREAT property managers that immediately come to mind, one handling 5 high end high rise condos I owned in Phoenix and the other one handling a 12 unit very lower end apartment building I owned in Arlington, Texas.  

This could lower your resale value. 

If the loan amount you are looking for is small relative to the value of the first and the second property combined, they are very well secured on a LTV%; ask for a 1% point lower rate.If you don't want to Cross Collateralize, do you have any CD's or MM you can transfer to this bank as collateral. 

My question again stems around using seller financing to allow them to receive a consistent monthly pay of X amount and delay/lower their tax bill in the short term instead of going through a lender to borrow 800k+ causing my mortgage to be significant part of our income roughly 40-50% of take home -  which we are approved for LOL.

That is lower than market and puts you in a cashflow-neutral situation, but it is unlikely your residents can afford that.

Well that is when the lower tenant feels like paying her 20% portion of the rent of $240 per month lol!