Then, I plan to purchase an SMF property that cash flows and repeat that process a few times over until I am able to generate enough income to reinvest to replace my main source of income today.Any specific neighborhoods in the WPB you think will have the best appreciation in the next 10-15 years? 

But they even stop and chat with me while I'm up cleaning and I'm able to check on them, make sure everything is good and see if anything else needs replaced like TP, paper towels, etc.

(Roof, box gutter repair, outdoor concrete stairs/walkway replacement, HVAC replacement). 

We wanted to find our path to replacing that income and not sitting in a corporate cube 8-10 hours a day.  

If buying a condo research the HOA health, engineering study, last 5 years of HOA board and meeting minutes and last three years of HOA financials/reserves. 

Just look at your insurance policy, if you have insured the duplex for replacement value (and not for cost) it will show something like 400-500k. 

Since someone is breaking a contract, you actually don't have to let them out of it, and you can hold them financially responsible for the rent until you find a replacement tenant. 

Utilities, site upgrades, engineering?

We got the house dirt cheap, no utilities were on the majority of the rehab and we replaced everything.

For furnishing short- or mid-term rentals, finding the right balance between stuff that looks good, but which also offers solid durability and keeps your budget in check can be difficult.If your budget is your driving factor with your design decisions, I'd start surfing on Google image search or Pinterest - find a picture of a finished room that you like, and then reverse engineer it from products on Amazon and other similar budget-friendly sources.