As a side note, we need to repaint in the spring as the paint on the wood siding is in rough shape (roughly $4000-4500 in all).

Wow, those pics of the repainted countertops actually look pretty good.

We repainted it this weekend and are having the carpets professionally cleaned.Policies - I haven't even got to the point of talking about policies.  

Its hard to tell on the walls as it seems they tried to repaint them the same color.

I'd rather have worst case scenario like replacing the entire carpet or floor or roof, repainting the entire outside, etc... but how much do those usually cost?

Also repainting interior walls and cleaning carpets after 5 years is generally considered  "normal wear and tear".

The rent is still about $100 below market but the place is rough and would require a lot of rehab.They agreed to the amount quickly but then asked me to repaint walls and re carpet the flooring if they sign a new year-long lease. 

If you've damaged some of the paint, you'll pay to repaint the entire place.

Im working with a seller now, and several issues we are addressing is changing out the mailbox (It is the same mailbox every $400k renovation uses, which wont fly in the $600s), changing out kitchen cabinetry hardware, kitchen faucet, repainting some rooms, and tearing up carpet in the basement to lay down a tile floor.  

If on the east coast, you will need to repaint the home and replace the HVAC system every few years. the salt and sand have extremely detrimental effect on the house and the upkeep.