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.

House needs to be painted before i can show it, and she is not allowing to paint.

I suppose the picture is painted rosier at the beginning..But maybe that's the expectation in the Detroit market.  

We painted, replaced flooring, added countertops, fixtures, and bathroom finishes.

Rather than painting the entire exterior, including the house, garage, windows, and doors, in one color, try a two-toned approach.Don’t forget the small details!

I hired them to rent out my condo/apartment and was told that a “professional photographer” would be coming to take pictures, instead a man came with 3 small children that were kicking our freshly painted walls/trim while he snapped pictures with an old phone.