I normally advise that people start a business as a sole propeitor in their first year.If it is successful and something you want to continue, then have a conversation regarding entities.

Yes, it's not a bad idea to keep things in separate LLCs, especially when you own them outright.

I encountered issues opening a bank account for a Subsidiary LLC as well.

It sounds like you’ve built a strong foundation with your first rental—locking in a 2.25% interest rate and pulling in $4,500 in rent is a great position to be in.

Find a great, local lender who knows the VA program inside and out.

We will be the only or one of a few that we can see with this type of amenity in our market for a vacation rental.

I've used this strategy in a similiar situation wherein the repairs needed to the property were made part of the agreement and the tenant buyer took possession with repairs needed and fixed the property to livable condition.Also in the scenario I received $5.5K down payment on a 3 year term $1200 per month and P/I cost me $550 and I paid taxes and insurance. 

We have gone high as 97% the only 100% I have seen is from a company called Kiavi. 

SBA lending has gotten a bad reputation over the past decade.Ask around, and you’ll hear the usual complaints: “Too slow.”

He's a CPA/CFP and is well versed in this area.