In case you haven’t read the previous responses or haven’t walked a mile in a landlord’s shoes. 90%+ of your problems are caused by your local/state government that you seem to be giving a free pass.

There is legislation pending that would allow it to be done without a City Council Ordinance, but it's unclear if this legislation will pass. 

If you’re right and this tenant would have passed their screening.

My first MF I represented the buyer on I made 100k. for maybe a weeks worth of work. 3. if your going to be looking a more resi style duplex 4 plex a lot of those get listed and having access to the MLS is far superior to any other on line listing service ONE simply because you will be able to talk to the actual LIsting agent not someone paying for leads.And then of course having access to MLS lock box's and not relying on agents.. this is huge.Now if your maybe going to buy one property sometime in the future and you have no interest in learning the RE laws of your state or making any money with transactional real estate then sure.. its a pass.. although I would still recommend the pre license course so you learn the basics  the vocabulary and states unique laws.. knowledge is power in RE.

the one with the baby passing away that will be something.. 

Look into how your county handles properties of deceased residents who pass without a will or trust.  

When you say your house hack phase has passed, are you saying you DON'T plan to occupy a unit of the 4-plex?

We converted a old restaurant on the property to a coworking lounge, redid the pool and built out the roof to a entertainment center with fire pits, lounges, bubble chairs, barbeque, large screen TV, music, yoga mats and amazing views of the ocean and city lights.It is designed for coworking/coliving for business professionals and entrepreneurs who want to...Live where they work.

Mention a payment schedule that reflects project progress and key milestones, such as rough inspections passed or drywall completed.

Some sellers will still entertain them.