I don't see a 401k/IRA as a competition with real estate as with the correct setup, you can self-direct 401k/IRA funds into real estate.

I really enjoyed san juan, but realize it might be the most competitive area.

With fees doubling and competition heating up, you might want to rethink this investment.

To me STR and hotel caters to different groups of travelers and so despite competition as long as the travel demand of Hawaii remains (as you pointed out is a robust assumption) I think both will continue to do well.  

Assuming the Oakland rental market continues to remain stagnant/competitive with newer buildings going up, is property appreciation the only way to increasing wealth with my building?

Southwest Florida is definitely an exciting (but competitive) market, so props to you for diving in!

I have heard that CA is very competitive and very difficult to find deals in.

Reduced competition and higher prices for renters.RealPage, of course, denies this.

.- The 203(k) will allow you to bid on properties that need repairs that won't qualify for a traditional mortgage => less competition => better purchase price.You will need to find a great local contractor you can trust to supply the required bids to qualify for the 203(k).- After closing, you can do some of the work yourself to save money, but the program doesn't allow you to pay yourself.You will want to buy a Class B property, maybe Class C+, in an area that seems to be improving.

If rates come down at all I predict we’ll be back in a strong sellers market (competitive offers, steep appreciation etc) because inventory is still low.