If all major components in the property are new (or recently replaced/upgraded) and you don't have to worry about them for a few years, then not as big of a deal and you can building up the rainy day fund.

Of course majority of lenders that provide VA loans does not have a time-frame on how long you have to occupy the home.

Last month I had major needing to evict tenants and do a major cleanup and fix several items after they trashed my place in less then 2 years.

I use a marketing strategy that puts properties across the MLS and all major channels, including social media, craigslist, and the usual Zillow / Trulia etc.

It also concerns me that the majority of your STR market is golfers, I am looking for something that has the potential for year round rental potential.

They will use threats, coercion, fear..every kind of tactic to stay rent free. 

@Brian Dvorak Hey Brian I'm looking at a burned house in my area and was wondering what major factors do you consider when you flip burnt properties?

Are you directly referring to issues with bad tenants or issues with major property expenses, or something else?

Well worth the cost and effort.Going from 5 to 20 properties would be a major move.

You are better off analyzing the remaining life of major Capex components like roof, windows, plumbing, furnace, AC and have a reserve fund set aside as part of acquisition cost.