You should also realize that investing for appreciation is a speculative endeavor no matter what historical data looks like.I would also say that landlording is harder than it seems and if you are tied to other obligations, a negative cash flow property could teach you the strategies and methods of landlording without burning up a lot of your time if it's a nice place and it's close to where you live.I agree that looking for opportunities out of area is a good way to have the best of all worlds.

@Max James   unemployment sky rocketed  renters defaulted like homeowners this led to a huge melt down in values in most of the heavy rental areas .. along with the markets were rampant speculation was occurring ( think Vegas  FLorida  PHX and central CA.)

So unless the land is what we used to call a "tax payer", i.e. being held as a speculation for a large increase in value, I don't see this deal as being very good.Income from the rental of developed spaces is preferable to income from renting spaces and homes, for the following reasons1.

These are guesses by the HOA at this point as they do not have real numbers or even timeframes as of now and are speculating but these assessments will cover new windows, patio doors, and siding - items that do not really add to property value. 

Once you find 20+% equity, whether from appreciation (speculative) or loan balance pay down, you can re-fi the equity as down payment on a conventional loan and then utilize the VA 0% down again on another property.  

@Kyle JosephJust speculating, but STR rates may go up in the near future.

If speculation is what your looking for, then consider it. 

At that point you are banking on speculation.

A LOT of foreign national speculation in Ohio FYI.Happy investing!

Another con is you have to make your own speculations about the area to determine if its worth flipping.