However, the risk of significant repairs is not to be taken lightly. 

Plus for its high cash flow potential, utilizing a 1031 exchange to reinvest gains effectively made this experiment a relatively low risk for me.

Fix-and-flip or builder’s risk insurance should be in place before work begins, and confirm your contractor obtains all necessary permits to avoid delays.

This is personal opinion and could be wrong so use at your own risk.1) Yes, it is possible to find deals where all of the cash flow for 5 years (and often more) is offset by depreciation. 

It does later say in the agreement that it is:"binding upon persons who own, lease, sublease, or occupy any parcel or portion thereof"The inclusion of which seems to imply that long term renting and/or subleasing would NOT be commercial use.I'm trying to figure out if I'm taking a significant risk buying this property for use as an STR.

It would be a direct sale with no brokers involved. 

Transferring mortgaged properties to an LLC may trigger due-on-sale clauses, but transferring to a trust first can mitigate this risk.

My risk appetite is 80%.

However, I’m hesitant due to the risk of the chatbot going off script and potentially leading to discrimination claims.

I also got involved with a builder in Florida who has yet to produce the first of three houses they're contracted to build, which was a major hit to my available funds as well, setting me further behind.I also figured if I fell a little behind in saving (18 months instead of 12 months for example), I'd still be making progress.