I'm only bringing this up because you mention 1) rent is always paid on time; 2) neighbors have no issues; 3) The tenant's are hardly there (which means less property wear and tear) and 4) I will also assume becuase of the first 3 here, that your property is also being cared for...... seems like picture perfect Tenants.... 

But people seem to rarely be held accountable either for malfeasance or neglect anyway, in both fields. 

I have been using propstream for single family but it doesn't seem to work well for land deals.  

I ended up looking at the planning documents and it seems like the s8 units will be there for some time.

I sometimes think about becoming a GC myself since all the ones out there seem to be really bad.

So sustained maintenance should not be your concern, your concern should be on how fast you can recover the initial cost of the hot tub, the maintenance is not the issue.Argument #2 Seems like this is based out of fear and the unknown.  

Does anyone have advice after looking at homes it seems impossible?

I'm paying neither up-front commission (my brokers get paid by the DST management) nor ongoing commissions.That seems like a pretty good transitional investment to me.

However, it seems like there are so many rules and regulations with the State/City and when it comes to getting approved to list on Airbnb. 

You make a lot of claims but don't seem to truly understand microeconomics.