do not get carried away, play conservative on your first deal, leave some room for error.3) Find a qualified and experienced contractor, do not settle for cheapest, you want experience here, because their is a significant administrative burden not only paperwork, proper formatting, but also financial constraint on the contractor as these sometimes have $0 prepayment to contractor.

I think you might drown.If your scheduled rent is $2025, you need a vacancy allowance (8 - 10% is a good range unless you know the area well and know the prevailing rate).This brings you down to $1823/month effective revenue.Then you need your operating expenses: maintenance (10%), landscaping, utilities (electricity and gas) for common areas (i.e. laundry), property management, administration, advertising, pest control, etc.    

Without knowing or understand your entree scope of work, if you have more than just paint consider using a 203k certified contractor you can search the 203k contractor database, these contractions will have the proper knowledge in place to be able to assist you with what you are seeking along with completing the administrative paperwork. 

I don't know if death being the reason for a change in the household makes any difference...Section 8 program administration details seem to be quite local, so double checking is the best thing to do!  

Employ a process for removing the outgoing tenant from the lease and charge a reasonable fee for this administrative work.

He would GC the project, and I would help on design, fixtures, and management/administrative items.  

You wouldn't want to get hit with fees or fines for not knowing something that turns out to be super important.Once you feel knowledgeable about the rules, find a good administrator who can help you navigate the ropes.

As you alluded, a rooming house can be lucrative, but it will be more administratively involved than letting apartments.We rent furnished rooms and provide dishes, cookware and appliances in our kitchens.  

Convention would be for the borrower to pay all origin (loan preparation, legal, appraisal, etc) and administration fees (i.e. the servicer) during the course of the loan.  

Start by contacting the Section 8 program administrator for your area, most likely a Housing Authority.