Regardless, guy did a great job so not going to complain about order of operations, but I am in a bit of pickle. 

There are also additional costs of operating and maintaining an LLC, like separate bank accounts, annual report filings, tax filings, etc.2.

If it's currently an STR they should be able to provide you with the p/l statement from prior years so you can see gross rents, operating expenses, average daily rates and occupancy levels.

I will say that even though you get the boost from VRBO and AirBNB, the first year of operation is usually lean as you build up the rep.Offering a discount on the stay is a way to be more attractive but don't go crazy.

Beyond that, will you operate as a partnership?

The "easy" answer - short term rentals where your brother participates materially in the operations - this would mean 500+ hours a year.It sounds simple from a tax planning perspective. 

This will create your new basis.From an operational perspective, you might want to touch up a few things on the place to make it more rentable. 

Landlords mistakenly ASSUME all PMCs offer the exact same services and operate the exact same way, so price is the only differentiator.So, the first question they usually ask a PMC is about fees - instead of asking about services.This also leads them to ASSUME simpler is better when it comes to management contracts.

-The mention of syndication being less risky than HML...I'd suggest it is more risk, possibly much much more since you don't know whether you are good or bad at vetting the operator right now.

I find it a great way to earn additional compensation as long as its a deal I like with conservative leverage and strong operators I trust.