In PR, understand the locals disposition to OOS investors, even those fluent in Spanish like yourself (or so I gather from Spanish language interview questions).No harm in beginning the interview process with both lender and agent today.

Your local housing authority will publish a list of market rent based on the size of the unit. 

Ask this question to the local people in your area.  

Does anyone know a local credit union or bank that will fund a HELOC on an owner occupied duplex?

There are lots of meet up groups around Orlando, you'll have to travel a bit for most of them, but if that is your goal...Also check out CFRI dot/net if you would like to network with other local investors and trades.

It could also be that your rehab/finishes/curb appeal are not up to local standards to attract the buyers but price overcomes all objections.What can you do now and next time?

Get pricing from your local builders to make sure the build costs are current5.

I don't plan on buying anytime really soon but I'd love to start connecting with more seasoned investors and local professionals within the area.

OOS investing is a lot harder than advertised.if you pick a local or local-ish market you can spend time in it, walk properties, go to REIA meetings, build a network.

It depends on your local laws, but any paperwork you can provide the tenant to indicate that they need to respond might help.