The other side, in the guest bedroom was painted dark gray, and downstairs was left exposed as well for an industrial feel.

So, you are filling holes and dings and touching up paint anyways.

Interior - Recently redone black granite countertops in kitchen, but original cabinetry was simply painted white by previous owner with black accented handles.

If I am doing the security deposit I want to quickly see how old that carpet or paint is.

Faded paint?

Plan is to wall it off and convert to a 4br/2ba,  update existing bath and kitchen, new floors,  interior and exterior  paint.

Is paint enough or is all the trim rotted? 

Would need some cosmetic (paint, refinish floors, minor repairs/upgrades completed by me).

I've been slowly updating -- new kitchen and bath in one unit, Fresh paint throughout, etc

For example, if an HOA establishes a rule regarding exterior paint covers, deed restriction enforcement would be with that HOA.It is important to be aware that liability for breaking a covenant rests with the titleholder to the property, even if that individual is not the one who technically engaged in the deed restriction violations.