I feel like a gambler who got pretty lucky in Austin and I would like to get out of there while I'm ahead, as it is still a correcting market and houses are quite expensive.

Pre-understanding of the area/market, willingness to fix and live in an outdated and damaged home.

Goto some networking events in your market and see about teaming up with local investors on your first one.

If you have the money, and are asking the question, I would say you are ready.The only other question might be - are you timing the market right?  

Note, Jacksonville FL is the largest market (area) in the nation and fairly nuanced.

My expertise lies in the vibrant market of Pinellas County, where I've honed my skills for over 7+ years.

The stock market has been on a tear this year… so if you could make 25% on your money in the stock market (as has been the case year to date), you are better off leaving your mortgages in place and investing the money in ETF’s, etc.  

@Karl KauperManayunk, East Falls, Roxborough, Fishtown, Northern Liberties, and University City are safe neighborhoods with diverse populations and strong rental markets.

I see virtually no chance that it does not outperform the general San Diego market which historically has outperformed 90%+ of markets.

I'm particularly passionate about off market deals and adding short term rentals to our portfolio.