I can personally repaint most of the walls and touch up the rest but that only takes care of all the patches.

The walls had to be repainted from the holes, smoking and misc stains.

You can take a piece of crap and repaint for cheap and put some gloss on it.

If it's more of a row house, you have a lot less yard to work with, so I would concentrate on simply making sure the yard is need and clean, then focus your energies on the front porch and front of the house.A few must do's for selling or trying to get the highest rent...Power wash the porch, front of the house (unless you have repainted) and sidewalk.  

About every 2 years I have to strip the wood and repaint. 

However, she did have a few requests. 1) She wanted the exterior of the house repainted because it was an eyesore. 2) She was raising lot rent to "market" which would make it $420 a month!

I see many fail in this area because the cash flow on paper looks good but when the tenant destroys the place and you have a $10k bill to repaint and redo floors and fix cabinets etc.

June 2016 repainted the interior and other minor maintenance in preperation for sale, however 2 contracts have fallen through and we are about to have our 3rd fail (with Possession Prior to Closing to make the situation more complex now).

What happens when you have to re-paint and replace carpet after having 1 tenant in there for just 6-8 months?

The whole parcel is good horse pasture that is fenced, though the fencing is in bad shape and will need to be repaired and repainted.