Don't get me wrong, he's a great guy, but a pain in the *** to deal with sometimes.

Pretty common.I would imagine that others that don't do this is because of it being a pain to move frequently.

Honestly, that's up to you, what your goals are, what your pain tolerances are, etc.

That last part is probably the biggest factor in my book, and what essentially currently defines the real estate financing industry: the cheaper the loan, the more painful it will be.

I value cash flow first and taking a large negative hit each month is painful. 

I want to add a bedroom on my primary and the list of things they want me to do would add about $10k to the project (and I already have solar, now they want me to add sprinklers but I have vaulted ceilings so that's not practical, they don't care) so I feel your pain on regulations in general.Of course it causes a knee jerk reaction whenever home prices are increased in a region that has a major housing crisis but I think the thought process being applied here is more long term (and I frame it this way because as I have said I have mixed feelings about the mandate, so I can only present what I think the policy makers intentions are). 

I'm looking to consult with a debt relief attorney.

You’ll be Replacing your carpet every couple years and it is a pain in the butt.

What about asking tenants if they have any pain points they would like to see addressed?

It can be a pain in the A$$ with the rehab restrictions and approval process but I see a ton of potential there especially with the continued gentrification of downtown.