@Kevin Connauton, I agree with you that although Pad Split is a great choice for getting the rooms filled, they don't cover all your bases in terms of property management.

My broker could not find any other carrier to cover a rental condo. 

The HOA covers all the exterior.What was the outcome?

Can try to reposition to Class B, but neighborhood may impede these efforts.Vacancy Est: Historically 10%, but 15-20% should be used to also cover tenant nonpayment, eviction costs & damages.Tenant Pool: majority will have FICO scores of 560-620 (approaching 22% probability of default), many blemishes, but should have no evictions in last 2 years.

We don’t know any PMCs to recommend in the area mentioned, but since selecting the wrong PMC is usually more harmful than selecting a bad tenant, you might want to read our series about “How to Screen a PMC Better than a Tenant”:https://www.biggerpockets.com/member-blogs/3094/91877-how-to-screen-a-pmc-better-than-a-tenant-part-1-services-and-processesWe recommend you get management contracts from several PMCs and compare the services they cover and, more importantly, what they each DO NOT cover.

My $2000 also covers stuff that inevitably break under normal use - I had to replace a washer $700, a stove $600, a microwave $100, and a grill $400, all  within last 2 years, and paid close to $1000 for various service calls by electricians and HVAC techs and pest control. 

Instead of evicting them, i was thinking is there some way that I could rent it back to him for very cheap (mainly to cover just the taxes/ insurance) ie 2k a year rather than the going rate of 2k a month for similar properties.

Insurance would cover it, I would pay the deductible, and no assets would be lost.If you are in an area like San Diego where people are more likely to sue, a judge is more likely to find you guilty, and the payout is expected to be higher, you may consider an umbrella insurance policy.

I did the math and could cover the mortgage solo if needed.

Insurance doesn't cover anything anymore and we can almost just pay for all damages with the money we spend on it!