1) The bottom unit is in a basement where half of the unit has ceilings above 7', while the other half are around 6.5'.

I put in steel beams vertically along one wall to "pin" the wall floor to ceiling.

There is a huge water stain in the master bathroom ceiling (see photo).

As I walked through the properties, I could see things like termite damage, floors that needed new subfloor, obvious need of a new roof, very old furnace or a/c unit I would never sell to someone in good conscience, foundation issues (like cracks going from basement floor clear to the ceiling, and other such things.

The ceiling height is ideal and the unit would have one egress through the basement door and another through a window. 

My opinion is that if either porch structure collapsed, it would wreck the house and hurt the foundation even more.The second biggest issue we have is half the walls and ceilings show sign of sagging because the plaster has come undone, this seems to be a pretty expensive fix, considering it's in both kitchens, and most bedrooms in both units.

Additionally, we will be removing 3 large chimneys from the roof down to the ceiling of the first floor. 

For example, basement ceiling height in the commercial code is 7'6", rather than the 6'8" for residential building code. 6) This will not be an easy project, but adding two units in Portland could quite possibly be worth the hassle. 7) If you have any intention to use conventional bank financing, do it now, while it's a 3plex so you're looking at 1-4 unit financing rather than commercial financing. 

I started with a bedroom: removed the trim, window casings, outlet/switch covers, and popcorn ceiling.

It has STOMP/STRIPPLE ceiling textureAnyone have any experience hiring someone to do this?