Searching through the MLS listings, my eye is constantly diverted away from searching for profitable properties to admire a Second Empire Victorian with a beautiful Mansard roof, a stately Greek Revival, or the sleek lines of a Mid Century Modern.

This scenario is usually only the case with mobile homes attached to land.Long story short is that you should fix the holes in the floors, holes in the walls, holes in the roof, fix the electric and plumbing if broken.

It was leaking when we purchased the property, but our best estimate was the last reroof was in 2004 when the latest addition was completed.  

Cost per foot/etc.)New roof?

It needed everything; plumbing, electrical, HVAC, roof, windows, insulation, drywall, flooring, all new fixtures.I had to remove the entire second floor and rebuild it; 2 bedrooms and 1 bathroom.

You don't want a special assessment for new siding or roof soon after you purchase.Matt's calculations are incorrect because he's using the $450/mo as the debt service, when it actually includes HOA & insurance.

I would spend the money to have an engineer do a complete inspection and have them include the expected remaining life of all the major systems, roof, HVAC, etc. in their report.Another area to look closely at is the commercial leases.

I cant figure out what to do with the exterior, I've thought windows siding, roof, landscaping.

Solid roof - sans over a bay window that needs replacing.

look into the spyder tubular skylight, you may be able to get both lights from a singular roof opening, and use at least a 6" high curb,,, see local recommendations and codes