They pay what's past due as well as several months into the future. 

I understand this is a personal risk decision and I'd love to hear pros/cons/things to consider from the Bigger Pockets community.

So it may be better to let someone else do the heavy lifting and take most of the risk (i.e. they be the sole guarantor on a construction loan, etc).

My view is there is risk in unpermitted work including getting caught and having to come compliant and/or not being able to rebuild if something happens.  

It seems as though several people are getting into the business of doing property management activities but calling it “co-hosting services” instead of property management in order to not need a Broker’s license.

Probably not...but is committing mortgage fraud worth the risk?

In my small town, both options can take several days to a couple weeks.If my washer goes out, I drive to the laundromat like any reasonable person would and deal with the inconvenience. 

I have several investors who absolutely won't make an offer unless they review the financials before hand. 

You could buy a multifamily, fix it up, rent out units while living in one, then refinance to pull out your initial investment and repeat the process.Additionally, deep-diving into specific areas within your target markets will help you identify properties with higher rental potential for your mid-term strategy.And regarding owner-occupying your first multifamily, this could be an interesting option depending on your financial goals and risk tolerance.

A family friend of mine who is a long time real estate investor with several properties has offered to sell me one of his properties.