The drywall contractor said that he would recommend getting a skim coat prior to re-texturizing but its an additional $2000.

yes, it could use a coat of paint, lolI don't care that much about the insurance company paying for the structure if it gets damaged in a storm.

The hot water pipes leading from the boiler were leaking in 20 places the inspector could see and as a bonus were wrapped in asbestos.2) There is only one thermostat for the building so the tenants on the top floors often open their windows during the winter because so much heat comes off the radiator, as a result the gas bills (landlord payed) can sometime be more than $3000/month in the winter.3) Some of the electrical panels had been updated but most had not and the wiring was all original fabric coated and would have to be replaced if worked on.4) The roofs needed replaced.I could probably use all of this to get the price much lower but it seemed like just too big a project to take on especially when the numbers were good but not great.Any experiences working with older properties like this?

Its a paint/primer combo home depot sells, and covers almost anything in one coat, and its very reasonably pricesPictures Here - https://picasaweb.google.com/115087615115568171260/Property1After?

I suggest that if you are rehabbing an older home with plaster walls stay away from them if there were extensive wall paper covering unless you are ready to rip the plaster down and do drywall or you can rip the paper down and texture because I have found that back in the day most people did not use sizing and the paper destroys the finish and skim coating is mucho dinero.

I hate to say it but you need thicker skin and that only comes with time and experience.

You use a diamond coated recipro/Sawzall blade and pause every 30 seconds to dip the blade in water.

It's fantastic what a new coat of paint will do!

I do epoxy floors and concrete polishing (Full Mechanical) and  I tell people all the time that the coating I put down is only as good as the surface it is applied to. 

I haven't stood in line getting paint mixed or paid retail for coatings in 12 years.This efficiency kitchen was painted with a $9 mistint and flooring re-done with remnant floating vinyl.