Ross:Here are my thoughts:1) "As is" basically says to me they do not intend to give a discount because you suddenly realized the roof needs replacing. 

That sounds like a good plan.

Hey John, Sounds like you need to talk with this person and question them on the benefits of real estate and what you can write off for your situation.

Sounds like you found a great handyman.  

Sounds like a JV agreement and then hold title with a lien maybe?

You can partner with an operator or hire a mentor to help you.Either way sounds like you have a good problem as most people struggle with raising capital so your already ahead of the game.

Replaced the water softener.

Sounds like the BRRRR method could be a could way to go about that if you're open to properties that need some TLC as opposed to ones that are turnkey. 

Financial freedom goes beyond simply replacing your current income—it's about sustaining your lifestyle for life.

The STR market—especially in vacation hotspots—can generate solid cash flow, and it sounds like you’re ready to dive in.A great starting point is to focus on researching markets.