To get this house rent ready, I will need to refinish floors, repaint many of the rooms, and update the electrical system from knob and tube, The largest unknown is an uneven floor upstairs from an addition but there are no indications that these problems are foundations or structural in nature.

I've got a painter repainting interior the week after. 

But, how many times do you think throughout that 5 year span will you be repainting units?

Completely re-paint interior of house including garage and ceilings runs approx $700 for labor.

And then the tenant moves out and it takes you 30 days to find a replacement tenant so you have no income for the month, and you need to repaint the interior costing another 2k.  

This is my 7th property but the first time we've done anything major like add a bathroom...is it reasonable to expect my contractor to re-paint wall that they messed up during the construction process or is that my responsibility? 

mainly cosmetic: stained floors, repaint, may need to replace carpet with hard wood, resurface cabnets, new shower, repatch water damage. 

Is this as simple as (1) install gutters, (2) install french drain, (3) use killz and repaint? 

If smoking does occur on the premises: 1) Tenant is responsible for all damage caused by the smoking including, but not limited to, stains, burns, odors, and removal of debris; 2) Tenant is in breach of this agreement; 3) Tenant, guests, and all others may be required to leave the premises; and 4) Tenant acknowledges that in order to remove odor caused by smoking, the landlord may need to replace carpet and drapes and paint the entire premises regardless of when these items were last cleaned, replaced, or repainted.

It has already been repainted and had roof sealed recently.