Great tools that get updated regularly.I am on the lending side of things and would be happy to hop on a call with you anytime to discuss financial strategies and help answer any questions you may have about nearly any loan product available to help you on your journey, even if they are not products my capital partners offer.I have quite a few clients investing in Ohio that are BRRRRing. 

I come from a poor upbringing and don't really have family members that have any money.

Quote from @James McGovern: I am interested in purchasing a few condos in Florida and want to understand if there are any insurance products that cover the rising cost of HOA assessments? 

Most lenders do not offer HELOCs on investment properties, so it may be difficult to find this product. 

Retiring when you are healthy and capable of being productive makes no sense.

It's a great starter book for the financial foundations of real estate investing: https://store.biggerpockets.com/products/set-for-life-revise...I would also recommend Small and Mighty by Chad Carson: https://store.biggerpockets.com/products/small-and-mighty-re...Real Estate Rookie: https://store.biggerpockets.com/products/real-estate-rookieHouse Hacking: https://store.biggerpockets.com/products/the-house-hacking-s...

My firm has a fix to rent product that discounts the interest on the fix portion, and discounts origination on the DSCR portion. 

In fact, if your tenant does poorly, it may put you in a situation where selling is the best option and you will be stuck using the agent that caused the problem in the first place! 

2> Terms and best practices: What are some ways to better set myself up to qualify for long term debt service products?

Keep diversifying your income with side hustles, and continue learning through books like "The Millionaire Real Estate Investor" by Gary Keller and "Rich Dad Poor Dad" by Robert Kiyosaki.By the time you're earning more, you'll be ready to dive into real estate, leveraging your higher income and knowledge to scale quickly.Let me know if you need advice on financing when you're ready!