For context, I will be assuming his VA loan at 5.1% and he will be doing seller financing for the remaining equity and sale price. 

I know you are dealing with a 3 month lease rather than a 12 month lease, but for example....Say I rent my home for $2,500 per month and have to lower my rate by $100 to find a quality tenant that is a loss of $1,200 over 12 months compared to a loss of $2,500 for each month it remains empty. 

Again, as with the question regarding the lender mentioned above, its best to ask your Title company if the insurance coverage remains intact if the asset is transferred.

In other words, STRs can remain and can be sold to other investors in the future3.

Short of selling my entire portfolio, the liquid capital for the down-payment remains unattainable. 

Would recommend you read a couple books about BRRRR, that will give you the basics and then feel free to reach out.It remains a great strategy, but you have to manage your expectaions.

So some ballpark numbers if everything remain the same, ($400ishx12)x10) would be $50Kish + the downpayment I see I got some positive numbers and after they are paid in full is when I believe the cash flow will be in better shape.I am planning to have all properties for long time, so I am planning (fingers crossed) to keep my primary income (job) in order to keep buying more properties.Once again, many thanks for all your comments.

Your payment may remain about the same as the original deal!

If the original mortgage on your building remains in place and is not part of the exchange, you do not need to replace that specific debt.

I'd like to see folks that are chosen to remain are vetted and documented.Soooo Don't bother arguing with me about what I see and know.