This is subjective, but I can see it when you're out to eat in LoHi or the Highlands or on Tennyson Street.

Is there anything I’m not thinking of that will eat up into my timeline.

The other complication is that as military personnel, we tend to be rank-conscious. 

@Ben Jespersen As @Drew Sygit points out above, $20K is not enough capital to make a direct real estate investment anywhere and especially in C and D class neighborhood where capital expenditures and potential tenant issues are likely to eat you alive. 

My favorite, they encouraged us to rip out our lawn and put in hardscaping to save water and be environmentally conscious.

I am conscious of that. and willing to change/adapt if necessary. 

We would eat the capital gains tax losses and fees from the sale, but we could hopefully match or beat the cash flow from CA property, diversify into several units, and have more room for appreciation.3.)

When I first started I was sleeping on an air mattress and eating ramen noodles and spending all my time learning about wholesaling.

Now flash forward about two years to where we are now, and the purchase price of a fix and flip in FS is going to be a considerable amount more in most cases than it was just two years ago- the numbers here might not make as much sense then in this case (it's certainly going to eat away quickly at your ROI).

The other state - here Florida - will still the taxes on that rental income, and the filing fees and time might eat up any savings that you might have if you were to just file as a New York entity.