What are your returns like, is it a strong STR market?

This seems like an odd strategy - purposefully invest in an asset that loses value, with the hope that it will regain value (so you at least get your initial investment back) all to save a little on taxes. 

I can tell from your initial post, that your former co-workers (...you've really got to love saying that!...)

If that's the case I would strongly suggest building your team before pulling the trigger on an Airbnb.

For the experienced cohosts in the group, I’d love to get your thoughts on payment processing options for cohosting companies (LLCs) that position themselves as property management companies but operate without a broker’s license.As an investor and soon-to-be STR entrepreneur, my business will initially focus on managing a small portfolio of vacation rentals with plans to scale. 

In Vermont, LLC formation fees and annual report costs can add up.A good friend of mine, Jason, started with five doors and used a single LLC for his properties initially.

Still strong but lots of competition, so you need to research what works: good pics, seasonal pricing, amenities, etc.

 - a study on rent cost compared to ownership cost shows that virtually every large city market it is initially cheaper to rent than own (I believe is was cheaper to went in 97 of the largest 100 markets)Miami and Florida have extra concerns:- insurance difficulties have resulted in large increase in insurance costs.  

To do so, I need an initial team who can cover the following aspects of these projects:- Wholesaler- Contractor (Inspection oriented)- Equity Partners (Project Incentives)Once the deals are in place, the financing support will be through personal capital for upfront costs, with the intention to raise private capital and include hard-money lenders as-needed.

My view if/when 10yr yield rates come back down to sub 3.75, there'll be a lot less dry powder on the sidelines after the initial euphoric lift which may be influenced by seasonality but will not show any real course of duration.