The simple things are roof, windows, siding/exterior, exterior doors, mechanicals, plumbing risers/laterals.

Home is brick/stucoo exterior, that is in decent shape-- Interior is a different story!

My plan would be to side the exterior, hang drywall (except a few accent walls), and go for a more trendy look.

@Kevin Reid This sounds like a decent deal depending on the interior renovations, assuming the exterior and structure are in great shape.

Regarding the exterior, is there anything in the landscaping that can be done to soften the "looks" of the driveway?  

There is a passage door along the closest exterior wall leading into the common area hallways. 

Once we started construction, we ran into several major problems including a steam pipe running through a kitchen wall that we were planning to open up, a huge leak inside a couple of walls that required the replacing of a whole exterior wall, damaged subfloors, major termite damage that resulted in a replacement of the sill plate in the master bedroom, needing to upgrade full electrical service (and split it into two separate panels) and a corroded water line that required emergency replacement all the way to the street in the middle of winter during record setting cold temps and a snow storm.

They're magnets for trouble and insurance headaches. 

From some articles I have read though it sounds like exterior upgrades tend to have pretty good ROI, replacing the front door with a nice new steel one in a color that works well with the house, and new siding (or stucco or brick treatment) can be quite a good improvement in the look, that usually has pretty good ROI.

-Type of structure and age, 2 story exterior corridor, 70's motel...etc etc....Do you have a photo?