No doubt that house hacking has become more challenging in the last few years but it is often still a much better option compared to both renting and buying a primary home just to live in.

Both times the tenants had renters insurance in place which took care of the issue so my client (the landlord) did not have to get involved nor make a claim on the landlord policy.We are very much in a hard insurance market right now - many carriers will not accept a new policy from you if you have a property or liability claim within the last 3 to 5 years (depending on the carrier) so you really don't want to make a claim right now if you don't have a large loss or can get it sorted yourself.

I've got about 250k of equity spread across 5 SFHs that I've acquired in the last year.

The ones most impacted by last-minute 1031s are the title company not the QI. 

This seemed absurd on multiple reasons: 1) what if I changed PMs in the last 5 years? 

I also worked with Hoosier Custom Construction, Bryant Burdine, last year and it was the absolute worst experience we've ever had.

I sold 3 of these just in the last 45 days alone with very complex underwriting and it takes time to understand it but same strategy.

Lastly, how do I determine cleaning costs, insurance, etc.

Last year I pushed the button and bought a house in San Diego which I've been using as a short-term rental and it's been doing pretty well.

While most medical professionals are good about planning for the future, the nature of how contracts get filled and where that takes the traveler often happen last minute.