Here is a solid structure to consider- create a holding LLC taxed as a partnership (you own this entity, and it is set up in a state with anonymity to keep your ownership private) this LLC will hold special purpose disregarded LLCs set up in states where your real estate is located. 

My quick math shows this just barely breaking even.You also have to worry about the financial health of the HOA, potential special assessments, and what the HOA rules around rentals are. 

Amusement, outdoor (east of the Intracoastal Waterway only).Day Care Facilities.Any Use that is customarily associated with the Main Permitted Use or Special Exception.

The PM has not called to say they provided special refunds due to the Carona virus so I suspect the guests will be stuck with the charge if it does not get re-booked (hopefully the PM is not going to tell us that they refunded the money for a late cancellation).   

I’m a contractor specializing in residential and multi-family renovations.

Here are some questions:- Is it true that there are companies that specialize in condos? 

It’s really a case of specialization of skills and appropriate scale.

Loooong story short, my HOA: Can't afford to make the repairAre getting bids to fix the roofHaven't fixed it or done anything about it yet (it's now March 11th)Will probably ask for a special assessment in the near future and/or raise our duesThey have no real timeline for the repair and "thank me for my patience." 

Plus you have special assessments, HOA dues etc.

@Nick Bowes I agree with @Ozzy Sirimsi I have properties with those numbers in my portfolio but they required quite a bit of work and specialized skill to acquire, rehab, and now manage.