My partner and I invest locally, and we figured it would be nice to connect with other folks doing the same.

How much is he paying you monthly to use your land?

The idea would be to sell the lots to pay down on the short term mortgage until the house got fixed entirely.

So, you PAY them EXTRA for that.

Even if its cutting the warranty off, sticking to manufacture warranties, and saving the cash to pay for expenses when they come up.

I recently read in a book that suggested I should open a dual checking and savings account, and take the security deposits from my future tenants and store them in the savings account, then use the checking to pay the mortgage or maintenance fees.

I would be willing to pay the gap as a down payment and assume the loan at 3.875%.2) I agree!

If I set aside $8500 for it, and in 10 years have to pay almost $11.5k, I will be short $3k. 

The employment GAP isn't always an issue as long as you're now a W2 employee, can show 30 days of pay stubs (not self employed), and you can provide a letter of explanation stating the cause of the employment gap.For a VA loan, in order to use the rental income from the other units you'll need:1.

On Oahu the bottom line of buying in this type of zone is that you will pay higher property taxes and fees, but you have a lot more confidence that you'll be able to continue to operate your property as an STR for years to come.