We have upgraded this property a decent amount from an aesthetics and general cleanliness standpoint, and put about $7,000 of work into it to begin with (new countertops, a few appliances, new carpet, paint, and tree removal).

We have done virtually everything to make our units bullet proof (new floors, new windows, new fixtures, new paint, new counter tops, new doors, etc. etc.).This keeps us viable in the market place and keeps our maintenance calls to a minimum. 

I agree, the rent should match fair market value, but the unit could use an updated bathroom, paint, & other cosmetics.Are these easy tasks to accomplish while the tenant lives there or should I consider paying for them to live elsewhere during the reno work?

My contractor handles paint/tile/cabinets/ basic plumbing/ electrical/ lighting/ trash/ fit and finish / cleaning it up when done. 

From a short inspection, I saw no vacant units in current marketable condition, but one was getting new carpet and paint during our visit.

Does it need to be painted?

Do tenants and landlords really need peace of mind for lead based paint?  

House has been well maintained, fresh paint job, newer Windows and has a great view of a little pond across the street.

I have experience framing, dry walling, painting,  and finance.

My wife and I bought a four-family in Massachusetts, re-did the wood floors, painted everything, brought in new cabinets, and raised the rents.