But the HI market trends due to the supply/demand there made it an easy decision to hold, with the added advice of some.

I have a very nice venue available to me and id be willing to supply food and drinks for everyone. 

Fort Lauderdale, Hollywood, and DavieLately, each time I visit I see new high-rise condo buildings being built so I am wondering if there is any risk of too much supply in the next few years.

It's great you are setting goals for yourself, but remember banks will be hesitant to lend to borrowers without a steady, W-2 job.

In an active investment, boots on the ground are critical and you want concentration where you have a strategic advantage, which is usually your backyard ... if you want to diversify, then buy a passive investment like a REIT or S&P500 index fund and be done with it.2: 6-8% has been the long run average appreciation rate over the last 40+ years, and for almost that entire time it has looked expensive compared to other markets if going on price alone and people have been saying it won't keep going ... ask some old timers and look at the historic data if you don't believe me ... if you are talking about just this cycle, you may be right, but if you are talking long term, which is where your head should be IMO if you are getting into buy and hold REI, then I think the underlying supply and demand fundamentals are solid.

Some places in California had a big run up in prices before the crash in 08 but I would think the more remote rural areas were similar to parts of the midwest that showed more steady sustainable grown It may still be possible to find cash-flowing properties in Sacramento and Stockton.

Everything goes through cycles; interest rates, affordability, rents, supply of housing, cap rates, rental vs home ownership etc. 

I have a discounted building supply store In my area.

Or should I stay the course, hold steady and purchase a quality investment property with a strong ROI and then begin investing in stocks while building equity in the property so I can use a home equity loan in the future to acquire another property. 

The amount of foreign money flowing into these markets and the fact that builders only see a  profit motive in luxury units is eventually going to bite the construction industry pretty hard.As David Gudmundsen pointed out in a  recent episode of the podcast, rent-value ratios are a pretty steady guide to the foolishness of the market.