Nothing is a sure bet.

That’s the best bet.

Mordechai ChaimovitzTwo-unit owner-occupied falls into an odd category, really any 2-4 unit with a nice owner's unit for that matter.

From there, you can research through zillow/redfin whatever but your best bet would be to find an investor/agent (I a one but based in Fort Lauderdale) who can guide you through the process.

There are a lot of ways to crash and burn, so increasing the odds of succeeding long term should be your highest priority. you can always sell your local assets once you're comfortable managing rentals and ready for a market that better-suits your criteria. btw, kudos for being self-aware of your limitations.

But anyone who considers themselves a GC for hire, it's a bit odd they wouldn't first get their ducks in a row, it's quite easy.If it was me, I wouldn't worry about him not being licensed/insured, I would just make sure to vet him.

I bet you'll learn just as much (if not more) for about 1% of the cost. 

You're right in saying it's making me feel uncomfortable asking them to pay (which sounds odd).

In my opinion, that is a riskier bet because you have to have a big pile of cash for contingencies.  

If they have money and can compete on pricing, brokers will be the best bet.