There are still a ton of roofs with blue tarps needing repair/replacement and some debris sitting curbside.  

we just see new investors in the forums blown away when they hit their fix big capex - a new roof, a new furnace, a driveway repair, a couple appliances going at once. 

It couldn't hurt to call a couple attorneys right away to see what they say in terms of cost and suggestions for dealing with this quickly.In terms of mitigating any legal issues with your tenant be sure you are documenting every conversation you have had with the HOA in terms of asking them to make the necessary repairs.

You’re in a win win situation no matter what however I guess you would also want to take in account any major cap x repairs that might be coming up soon in the future you might want to avoid paying. 

The property is livable, but I am account for a pretty significant turn in 4 - 7 years of paint, flooring, and any miscellaneous repairs that the inspector could have missed since it was occupied.

Got into the home with a low down payment , made repairs, rented and refinanced to pay off line and eliminate the PMI.

Perhaps, they can get out earlier such as July so you have time to do the necessary repairs so you only have one month of vacancy.

I would say that the value he brings is finding the deals, doing an initial diligence, having a local team set up for renovations/repairs/property management as well as knowledge of the neighborhood.

Quote from @Basit Siddiqi: I personally would not buy real estate with a retirement account.There are just too many headaches that are not worth the potential increased return.Some headaches when it comes to investing in real estate with a retirement account1) LTV values are less and harder to find lenders.2) Potential to sell or partially distibute the property if you have to do a RMD(Required Minimum Distribution)3) If you run out of cash and have to make a major repair, you may be out of luck and have to sell.4) Having to potentially worry about UBTI(Unrelated Business Taxable Income)I would personally invest in stocks/bonds/notes with a retirement account.I buy deals with cash and use a ROTH SDIRA so there are no RMD's.I buy at huge discounts to retail.

You're using a company to manage tenant phone calls/inquiries and then send in vendors for repairs.