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?

based on what you wrote, the ARV isn't high enough for hard money to work. 

I witnessed several PMs go out of business quite literally overnight, leaving owners and guests high and dry.Here is what happens:  PMs take lots of money in from future guests - advance deposits - that is legally required to go into an escrow account. 

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).  

What's important - the demand for STR went up well before the first kick and stayed high for a whole Summer.Why  should Miami be different?

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).

In some areas of high taxes or insurance costs (like New Orleans, you may need to go to 40% of EGR).

If it's rent - PITI - CAP/OPEX it most likely won't cover your expenses if anything more than a few hundred pops up.With today's interest rates I would consider buying a property I really liked even with only $200 in monthly cashflow, but I would want to have high confidence there is high appreciation potential.

I highly recommend that you define your financial goals and have a clear vision of what you aim to achieve.Thank you!

I was happy about this but then the sellers disclosed underground oil tank on the day of the inspection, found out that half of the house’s backyard falls is wetlands that is part of a conservation area and high radon level in the well water.