I concur that this house looks like a total gut.
Off the top of my head...
I'd plan to replace all the windows. 'Round my parts, that's $179/window or thereabouts for vinyl Low-E.
I'd expect to rewire entirely or significantly to bring the house to code and as a safety factor. Hodgepodge wiring, IMO, is rarely worth saving.
Have you pressurized the plumbing? I'd expect most of the plumbing to simply go kerplunk on you the instant you put pressure on the lines... or at least for the shutoffs to leak horribly. I'd also expect the drain lines to be suspect.
Forget fixing roof leaks. If the roof is old and a-leakin' one place, it's probably systemic. I'd plan for a replacement.
You lack door hardware. New hinges and doorknobs do a lot to spruce up a place like that.
I assume your flooring price is 100% carpet. What about tile in the kitchens and bathrooms? Tile is not $2.39/ft after labor.
Your sheetrock price is pretty low. I figure about $13-15/board, at about $6/board plus mud. But then, I treat labor differently...
Speaking of labor - if you're planning for one sole guy, and maybe his helper, come in and do this job... I estimate that you'll get done before the sun goes supernova. Maybe. You've got an incredible amount of labor just in small things like doors, floors, and sheetrock. To say nothing about plumbing, electrical, roofing, etc.
If I've reverse-engineered your labor number correctly... It looks like you've simply said... 8 weeks of labor, 40 hours a week, at $25 an hour.
Simply put, I'm not sure that you've got nearly enough labor here. Especially not if you're using someone who is general-purpose, and not using specialists for things like electrical and plumbing.
I see in your pictures that there is definitely some carpentry to be done. In a structure that old, you're going to be running into dry-rotted wood, dead superstructure, and other nasty surprises left and right. You need a budget for carpentry, and most importantly you need a carpenter who is competent to work on a building that old.
Photo #5 looks like maybe that's asbestos ceiling tiles. You need to check into it... if that is asbestos, you need to factor for correct removal of the material.
With HVAC closing in on 15 years old, I'd probably plan for replacement. I'd also expect a new water heater to be a requirement.
Back to windows... without seeing them, I'd say you should probably count on, at the very least, reglazing them. Reglazing can turn into an enormously labor-intensive job all by itself. I normally just avoid that issue by replacing the windows.
Doors are the same way. Those are no doubt the awesome, old-school, solid-core 5-panel interior doors made of awesome and badassery.
They're probably also dinged, scraped, and chipped up. Consider the fact that to make them look nice, you or someone you're paying will have to spend HOURS AND HOURS with bondo, wood filler, a palm sander, and then paint to make them look good again. This can turn into a very costly endeavor.
On the flip side, a nice, new, masonite pre-hung door should only run you about $50 (At least, that's what it costs me) and should take a good carpenter approximately 10 minutes to nail in place. It can very easily be cheaper to replace old doors than to fool around with them for hours upon hours trying to make them look good again.
I can't quite tell from the pictures - is there a layer of plywood over the old floors, or is that luan subfloor? In either case, you seriously need to look at the floor from the crawl space and try to determine if someone in years past put that flooring there because the old floor and old joists had started to rot out for some reason.
If the original subfloor and joist are rotting... then hold on to your hat, because the whole thing is going to get seriously expensive in a big hurry and your cosmetic rehab job will have suddenly turned into a structural rehab job.
You need to seriously consider your dumpster cost. A job of this size could pretty quickly turn into more than one dumpster. (Actually, it's hard to do much with just one dumpster. Rarely have I run a job that didn't take at least 2)
Uhh, I guess I'm kinda turning this into a word-wall, so I'll stop now. Needless to say, you've got yourself one heckuva first project! I'll be most interested in your follow-up posts.