When you are ready, a solid investment can be found in almost any city at almost any time.  

But your premise is solid and doable.

LOLIf I was looking at the Ocean from the 18th floor in Waikai with a blended Mai Tia I'm sure I would singing a different tune,well this is a pro landlord pro owning rentals website so of course that is what the focus is on and what Most that participate are looking to do.. however as Steve was alluding to . if you can scale up to solid Class B units that can be professionally managed it becomes very passive short of that your right lots of moving pieces which if you dig being a landlord is just fine..   

You have to have a solid team around you!

100% get solid contracts in place vetted by an attorney experienced in REI.

I have all of the evidence and I am looking for legal help from someone experienced with HOAs.

This area is great for solid renters as the local hospital has a huge residency program so there are tons of young doctors looking for solid apartments and will be around for minimum 3-5 years.

Been doing it for 4 years with solid returns so it wasn't an issue.

Rules of thumb (like MAO) are great starting points, but in the end if the numbers were solid and stable, would you rather pay $188K, get the deal, and make $10K less, or not do the deal at all?

I advise you to take this time to make sure you get a updated rental agreement/lease between you and him, after you do the repairs; take a long, slow video and lots of photos of his unit (& the whole building- especially rental & public areas) LABEL & SAVE the evidence in a safe place (or two!)