The process of purchasing a property takes a little time, but typically less than 60 days.

The VA rules state that typically needs to be 60 days but can be delayed up to a year in certain cases.

In the last 6 months i've acquired two more short term rentals in the Poipu Beach area and completed a 1031 exchange.

Prepayment penalties- usually 1-5 year terms.

I don't know 100% if this is the smartest decision or best decision long term, but that is why I am here trying to learn and understand. 

Typically you'll need to bring a significant amount of cash in the form of cashiers checks to put the downpayment the same day.

I am curious to know what the typical fees are associated with the operator they refer you to though. 

If you have multiple collections resolving even a few small accounts can bump your credit score considerably, and is the best short term way to improve your credit score, in my opinion.

All of those are "part of doing business". 3 years, 7 Airbnbs and hundreds of guests later I'm still a proud host and a big fan of the mid-term / short-term model!

Rents per unit are about 1K for long term tenants, although I'm likely to do STR or at least a combination of the two.