Quote from @Kwanza Price: Hello, I just upgraded to PRO.

If they like to rob houses, they're probably not going to become a model citizen just because they rented your house.

Unless you have an immediate need for the cash I'd wait until I could pull out the extra $40k. 

If you consistently analyze properties, recognizing a good deal will be much easier when it shows up.

You'll likely also reduce your cost of living by moving to a stabilized apartment.Depending on the cashflow and debt paydown, you can use this strategy until you've built enough equity to reinvest.On the other hand, getting into a multi-family after refinancing will also help you build substantial equity to rinse and repeat in the coming years.

We like the short-term rental idea because we could stay at the property ourselves when we want - summer break, spring/winter breaks, etc.Our budget will be right around $1M or less ideally, and we would like a short distance to the ocean.How likely is it that we could find a property as described above and have it cover or come close to covering the mortgage? 

Non conventional just means the loan will not be sold to Fannie/Freddie so they do not have to follow those rules.

They are just going to use their 2nd VA loan to buy their next one while this one is tied up. 

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Just the same way the increase in the money supply from 1969-1972 was the cause of the inflation we experienced in the same way just a few years later.