Since owning the home we have a installed a new roof, and downstairs heating/cooling system, as well as repainted, fixed cracks.  

When I moved back into the house in the spring of 2017, we replaced the floors throughout the upstairs unit and repainted the interior of the house.

Long story short, we have determined that we will have to repaint the whole house because of all of the holes and not being able to match the paint.

I am thinking about removing trees, vestibule at the entrance, all signage/banner, replacing front windows, installing an overhang at the front entrance,  and repaint roof, soffit, and wall.Am I going in the right direction?

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.

The lower unit needs to be repainted and window coverings redone anyway.2.

For my units, the main issue is whether I need to re-paint and/or replace the carpet. 

We have a 6 month-1 year plan of replacing the entire siding on two of the buildings and repainting the 3rd.

It really depends on the condition and if the person smoked indoors and was a heavy smoker.You are going to have to wash all of the surfaces with TSP, chances are you will need to repaint (especially if they've been there for 10 years) and may need to stain block the ceilings before painting. 

Best part is the company you buy from usually does a 12 month touch-up to fix nail pops, wall cracks, repaint, etc.