If you buy a high-risk deal like this and your contractor drops the ball, you could be at risk for some pretty big losses. 

That said, I am exploring an opportunity in the Orlando area to invest in some condos in a great location, however, HOA costs seem prohibitive, insurance is obviously very high, and STR is usually frowned upon in Orlando, I am curious if there is a winning strategy out there folks are willing to with share?

You’re in a great position with high W-2 income, and your motivation to invest for cash flow and tax benefits is spot on.Since you’re just getting started, I’d actually encourage you to consider long-term rentals (LTRs) over short-term rentals (STRs) for your first deal (this is coming from my own personal experience in owning STRs).

Flipping in NJ can be tough with high entry costs, so consider house hacking a small multi-family as a lower-risk entry point.

Finding high equity distressed or off-market properties is not easy; it takes countless hours searching for county records that meet investment criteria + direct mail is getting expensive every other day that builds a trustworthy relationship.Welcome aboard!

That is high but also it's a cost your borrower should be paying not you.

My wife and I have built up some significant savings and are highly interested and excited to purchase our first STR in the near future.We enjoy the pan-handle of Florida as well as the Southwest coast (Cape Coral, Ft Myers, Naples).  

Living in Los Angeles makes real estate investing unreachable with how high homes are here, so I will be looking out state to start my journey.

Removing asbestos may cause more problems then leaving it.My first instinct would be to permanently cover it with new flooring High quality laminate flooring for example.

Plus, it often leads to high competition, poor tenant fit, and poor yields.