So, that makes a BIG difference in How you scale and what your personal “upper limits” are.  

Like you said, I want to seed different strategies I can implement with the limited capital I have.  

So, you are not at limiting your self when buying a new property.

This halts production for anyone that is that far along - you can't just pick up trusses at your local hardware store - they are engineered for the job via the plans. 

Hi Marc - Aircover offers some protection for damages caused by guests, but it’s limited and doesn’t replace having dedicated STR insurance.

I might try the “emergency service” which is $20 with limited data and just use that for the smart locks and ring cameras.

Quote from @Stuart Udis: @Robert Ellis Location Location Location...There is limited land supply in markets with high demand and high barriers of entry.

You have limited time as well.

.- Many of these HCOL areas also have strict limitations on AirBnB or short-term rentals... that do not apply to owner-occupants - thus allowing for extreme cashflow potential for house-hackers.

Very few non-owner occupied property policies guarantee full replacement cost - they typically provide replacement cost up to the dwelling limit purchased.