NYC laws around rentals—especially short- to mid-term—can be tricky, so you’ll want to avoid any compliance headaches.The biggest challenge with this plan is finding a rent-stabilized apartment that makes financial sense and actually gives you breathing room.

Positives are proximity, low property taxes, no income taxes, no weather events, very low maintenance stucco/tile structures, “young” properties (5-20 years old) 

You can hear real-world examples of how others have built their investment portfolio and (hopefully) learn to avoid their mistakes.4.

Since you're looking to expand into Florida and other states, I'd recommend starting by narrowing down your focus:Market Research – Florida has great opportunities, but each state and city has different laws, taxes, and demand drivers.

I'm not sure how attractive the numbers will be however when looking at HOA dues, insurance, taxes & the unpredictability of future costs with HOA dues.

We bring/offer the mortgage loan investment to the group & handle all the servicing, including chasing the monthly payment/insurance/taxes, foreclosure, etc.

I’m in the 33% tax bracket through my real job and this could be a big difference in taxes owed if we sold the property?

Your team can provide valuable insight and help you avoid costly mistakes down the line.5.

This is day to day spending, rent collection, tax/utility payments etc. (1) account for all security deposits, (1) account for parachute fund, capex items etc.

Consult your local CPA to calculate accurately and minimize your tax liability.