Over several years, I have worked hard to save up for a down payment, and I currently have $200k set aside in a money market account ready to be put to use.

Private remarks (at least in our MLS) can only be viewed by real estate agents, so I have a search set up in our MLS for the Private remarks as well. 

In the book, he discusses pricing in a different state over 10 years ago so the # s won't translate to Long Island.Regarding working with contractors, the short answer would be to consider a 203K or homestyle renovation loan.

@Michael Plaks has a great post on this topic.2 - Assess the value of those tax deductions to you: The value of a deduction depends on (a) whether you're actually able to use it to reduce taxable income and (b) your marginal tax rate.As an STR, assuming the average rental period is 7 days or less, key items to consider are: (a) material participation and (b) avoidance of "excessive" personal use.

Maryland is also considering making psilocybin legal (next few years likely).

Most of the time the availability of funds + skill set won't match for S Florida if you are a newer investor.

I know you were focused mainly on the financial (financial planners, tax professionals, accountants, lenders, and real estate agent) But you'll also need to consider the physical parts.

You need to set actual realistic goals, realistic being they key word, pick a market study it, study it again, study it some more than decide if the yield works for you.

The other thing to consider is the Condo association.

Check out my personal favorite, Set For Life by Scott Trench , or The Total Money Makeover by Dave Ramsey.3.