I'd get a pressure washer and clean the driveway, that way it won't need to be painted again-let it go back to the natural colour of the concrete or asphalt.

Tidbits of what we know:It sounds like 3 program participants would stay here (potentially alone without supervision, and plus we don't know the participants yet).The participants have a highly structured day where they would leave early in the mornings (the business states that they're focused on keeping these participants very active and doing things).The business also said that the house is kept very clean, as the state can do a surprise inspection at any time.Perhaps my first question is to Jorge from the OP - did you end up renting to the company?

A good handyman, contractor, cleaning team, and cleaning inspector, make a great Airbnb. - Amenities: not only for guests that stay, but for yourself!

Squatter has online claims to be in a gang and owns a 24 hour Carpet or flipper clean up company.

I would also include a weekly cleaning service of the common areas (again included in the rent, so paid for by tenants indirectly). 

property radar does this on the west coast .. not sure if they have gotten to the east coast yet.its a paid for subscription but its uber powerful with many many features and notice of defaults are one of them. 

FreedomSoft CRM is another powerful option that can make lists, market, and follow up as easy as a few clicks. https://freedomsoft.com/?

We find win-win solutions that lead to profitable deals by getting to know each other, figuring out pain points, and using our negotiating power.

I'm not a CPA (although I do know a great one that specializes in RE specifically) but you can run a cost segregation study to accelerate depreciation into the first year to help on taxes (although this is phasing out, but can still be powerful), and may help with your plan to do Roth conversions. 

The opportunity arises after a family member, who has a clean title and owns the home outright, let the property go down the drain.