There is a "sponsor exemption" but that only allows an unlicensed person to raise money but it cannot be more than 50% of their duties and the pay they receive cannot be based on how much they raised.If you have never raised $, a family office will be off the table as they typically want the company to ahve atleast $50-$100M in assets. 

Florida did just have back to back hurricanes but a proper master insurance policy and coverage usually covers that type or perilYou are facing a declining cash flow situation which is due to the HOA fee's so while there is still a profit and you have equity sell and look for a 2-4 units.

How does the transaction work between me personally and my holding company LLC?

All companies must apply unless you meet a certain exemption.

I haven't spoken with anyone yet, looking to see what companies will do the DSCR loan. 

I don't think it is a bad idea to find work in real estate somehow as it will allow you to be comfortable with being around it in general, such as a property management company.

I own an HOA management company in Hoboken and it's led me down this thinking-path as well.

Those companies you asked about are more for deal finding and direct contact to off-market sellers, is that what you are looking for? 

I will note though that lots of people manage multiple rentals without hiring a STR management company (myself included).

@Adam RossRecommend exploring as many sources as possible to get referrals AND cross-reference them to get as much accurate information as possible.Check out NARPM.com, BP’s Property Manager Finder (BiggerPockets: The Real Estate Investing Social Network), etc.Also, encourage you to learn from the mistakes of others - by reading posts here on BiggerPockets about owners not having their expectations met by their current Property Management Company.