Make sure you discuss and write down as much of the details and terms as you can to avoid harming the relationship if the business does not go as planned.

There's no harm in an extra 5 days.

Landlord additionally points out that he did rent to Bob and at the current market rents, so therefore Bob was not harmed or discriminated against.

If you just don't pay rent, even with notice that it's due to repairs needed, you're likely not protected from landlord starting eviction, which could harm you in looking for your next place.  

Anger can result in property damage and personal harm.

If you have cash when starting in this business, it can be pretty harmful. 

I'm also really glad that you didn't focus on style over substance.

If neighbors are harmed then they should prove the harm and seek compensation from the one who caused it.

Again, not universal to any/all people, but in general yeah I see it doing more harm than good. 1 serious mistake is all it takes and that can wipeout months if not years of that "savings" of self-managing vs staffing for it.  

I, to this date, have found literally, ONE case where it was proven that LBP harmed someone.