9) adding multiple ADUs or adding an ADU to a quad looses F/F conventional financing.

Quote from @Jay Hinrichs: I think so at least for the ones we read about on BP..I had the same experience total loss on multiple syndication deals So I am feeling pretty good about how we are doing..

The harder from a zoning, land availability and pricing it is to get a lot, the better the asset or location is.Tourism-  I would say no impact, to greater demand. 

Although whichever option you go with make sure you're also thinking about the long-term property value and what makes the most sense vs trying different angles now that negatively impact future resale/property values down the line. 

Quote from @Tod DuBois: Hostaway appears to integrate with the multiple channels - but I hate to do a software setup and learn it's not a good place to do what I need to get done (which is work as little as possible and optimize my occupancy).

If you want to work with multiple agents, those agents know there's a very low chance of ever earning a dime, so they won't waste their time.Agents do much more than find property.

If i sell my SFR rental for $450k and equity is, for example, $200k...Can i invest 100k into a new SFR worth $275k and invest the remaining 100k into a sponsored DST or TIC (which deals are usually multiple hundreds of thousands of dollars?

Carnegie Mellon creates “$2.7 billion in economic impact each year”.

If you determine that the numbers look good, make sure to check other sites to see if the comparable property is on multiple sites that may add to the numbers.  

The city has changed Section 8 requirements multiple times lately.