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

.- (more and more municipalities are adding anti-STR regulations- you are competing against so many other people who want to jump on the bandwagon- you have no real control or authority on the properties you manage- you will be held accountable by the real owner and by the renters - but no deep pockets to handle issuesSeems like a niche that is being squeezed out. 

If you held them less than 1 year you would pay at your income tax bracket but if you held them over a year you would pay LTCG (Long-term capital gains) which for most people is 15%.You'll always be able to add money back into a brokerage account regardless of whether it's the LLCs or your own.Hope this helps

Any insight on how title is held on initial purchase? 

They could claim "something went missing" or was damaged by the worker so that they are not held responsible when they move out. 

But there since the zero basis in a long held property will either have to be taxed, or transfer that zero basis to the next one,  there is no magic in "rotating". 

If you held for the 10 years of cashflow, you would also have 10 years of appreciation which will likely surpass the amount of cashflow (vs. if you 'cashed out' and held cash).

Do you have any stocks held in taxable accounts?  

My plan was to add a kitchen/kitchenette to the addition after the city signs off on everything and rent it out as it's own unit But now that I think about it, if something happens in the addition (i.e, a fire) I could be held liable since that area was never permitted to be its own rental unit or have a kitchen.

I THINK you could have sent the note to the QI and then replaced it with your own cash and held the note personally to avoid that tax.