I can do all the basic things like lawn maintenance, snow removal, painting etc, and some electrical and plumbing.

Project included new windows, doors, siding, floors, bathrooms, kitchen paint, pool liner, landscaping.

My plan is to stabilize the side I purchased with cosmetic rehab (flooring, paint, cabinetry) before working with the owner of the other side to purchase it and do the same.

You would want to wait on or expect to redo cosmetics, paint, carpet, etc.Keep in mind doing remodel work that it's like doing a flip your not doing it for your tastes but a large group of people. 

Even though they were not his tenants they sued him for lead paint poisoning and won a multi-million dollar verdict against him.

This is a conversion from a 1 bedroom to a 3 bedroom, so not a simple clean and paint.

Our existing home will need to have some minor repairs completed prior to attempting to rent out - paint, drywall repairs, etc. 

I've read (all my knowledge is theoretical) that tenants on government assistance can be really rough on properties (I also see that as painting with a broad brush) but the government assistance side of that is pretty stable income, and it doesn't seem terribly difficult to raise rent either, just requires 60-days notice instead of 30. 

I am in Baltimore and lead paint lawsuits are a big issue.

If you request a lead paint inspection and lead paint is found in the unit, a landlord can remediate (remove) all positive lead-paint components and be re-inspected.