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. 

The Port Charlotte duplex...given it hasn’t suffered hurricane damage...could command a pretty penny on its own.I recall reading a piece in Forbes that suggests certain Florida markets could remain strong for years, which might help you gauge whether now is the right time to sell.

Most of the easy "lipstick on a pig" transformations are gone - you're often looking at more serious rehabs to make the numbers work.That said, we do have some advantages: strong rental market (lots of students, young professionals), still relatively affordable deals, and good appreciation potential in many neighborhoods.

Sounds like you are in a pretty strong financial position.

I strongly encourage finding a fairly priced, knowledgable accountant you can trust. 

Prioritize properties with strong rental potential and set aside reserves to handle unexpected costs.Finally, familiarize yourself with tenant laws in your target market, especially in Portland, and consult a real estate-savvy CPA for tax efficiency and legal considerations.

It's affordable and offers strong cash flow potential.

Since you're investing from a distance, I recommend interviewing multiple agents, lenders, property managers, contractors, and other professionals to build a strong and reliable team.

If you’re serious about this aspect of real estate and you have the time/money to invest into your education, I would strongly recommend Raisemasters as a quality mastermind to join. 

As an investor here myself, I can tell you we're seeing solid rental demand here thanks to the strong job market and major employers developing here.