At a high level it will all come down to the specific piece of land you are looking at.  

And I don't think it was a very serious offer, it came up in a conversation about selling my team, which is absolutely not on the table. 

Here, we will focus only on a December-specific question: how can I meet material participation if I buy an STR in December?

Specifically, has it changed their tax preparation bill since they can't just send their Quickbooks file over to their CPA?

HI we are Canadians investing in the us we  invest in Detroit and toledo where we have great teams on the ground including trusted property managers who take great care of our properties.

I can send you a list of contractors to help build your team.

Owners mistakenly ASSUME all PMCs offer the exact SAME SERVICES and PERFORM those services EXACTLY THE 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 and HOW those services are executed.EXAMPLE: PMC states they will handle tenant screening – what does that specifically mean?

But this year, his team is saying I need to file 1099s. 

ALSO they have regs on rooming houses only allowed in specific zoning, similar zoning as for hotels;  only on main streets in business districts AND you have to apply for licensing and blabla as for a hotel..That said;  there is a small movement supporting rent by the room as a small step toward solving affordable housing. 

The city just passed a very confusing zoning regulation restricting student housing to a specific area, and we're all trying to figure out what the fallout will be.