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We painted our whole house over last summer before getting our floors refinished. We are in the process of installing new trim now! So a fail for you, we painted our ceilings (a tinted color not just the basic ceiling paint as it was too cool and we were going for warm tones), to prep we taped up the walls with plastic so any drips wouldn't leave marks on the wall. After painting it looked great so we took down the plastic and tape, and painted the walls. Then realized the ceilings were a little splotchy so we had to retape and plastic the walls because now drips would have been a huge deal! When we took down the tape, it took the wall color with it! It was so frustrating. We didn't buy cheap primer or paint so I have no clue what happened. Anyway, do you have a staircase? Ours has a landing so theres a spot that is two stories and we hired someone to paint the two walls, we tried but didn't feel comfortable on our rigged scaffolding!

@Mrs. Oreo: are the walls and ceilings in good shape already? Our walls had a lot of nail holes and wall paper and things like that so prepping too way more time than painting itself. I agree with taking it one room at a time. Otherwise it'snot that hard, just time consuming. And get some good trim brushes- I liked the one Young House Love recommended.

Good luck! Second that the prep work is very important, and would also say it can be as time consuming as painting. Are you going to have help from his family? With a bunch of people, each doing a different job (wall cleaner, drop cloth-er, taper, wall painter, trim painter)

If you will be taping off trim, etc., I reco:
-using Frog tape
-locking the edge of the tape by painting over it with white paint first. then after it dries, painting on your color. Helps keep it from bleeding under the tape and gives a clean line.

@Mrs. Oreo: I read a couple of blogs (YHL and Bower Power) and I know when YHL moved into their most recent house and they painted a whole bunch of trims and doors, they invested in a paint sprayer to spray all of the trim and ceilings before doing the walls because then the didn't have to worry about being too careful with the trim.

Here is a post where they talk about their process
http://www.younghouselove.com/2013/05/buh-bye-blue-trim/
Might be worth considering if you can just cover the floors

We just painted 2,400 sq feet so smaller. But we did it in a system. I washed all the ways. Then DH primed all the ceilings. The next day we painted them all (BM Simply White) and while we had the paint out we did the trim. We let that dry over night and then we went room by room painting the first coat and then the second. Where we taped it turned out like crap so I took my time and went by hand.

@Mrs. Oreo: One other thing we did was use old baby food jars. After we were done painting, I poured just a tiny bit in the jar. When we needed a touch up spot, I had a little paint I could easily grab and touch up with.

I never tape after having a bad experience with it. Even when I was painting cabinets, I just went really slowly and cut in by hand.

This tool is ingenious for edging. And it's also super helpful for getting into tight spaces (like between a vanity and the wall) where a brush or roller won't fit

ETA: This is a better link. Shows how it works. http://www.homedepot.com/p/Shur-Line-4-75-in-x-3-75-in-Paint-Edger-Classic-Design-00100c/100070177

We've done this several times. Right now since I'm pregnant, DH is doing the whole house by himself . Just walls no ceilings though. We keep it manageable by cutting way down on prep work: all we do is remove wall plates. No taping! DH learned the "cutting in" technique years ago and he's very good at it. And we go for light colors so no need for primer or second coat. A room goes pretty quickly that way.

We don't use drop cloths either. Just pay attention and wipe if you see a drip. DH painted an entire playroom on Saturday with no tape or drop cloth and the wall-to-wall carpet is unscathed. Easy in easy out.

Second the saran wrap in the fridge tip -- getting the cans out and clean up is a bigger hassle than painting itself, and it's convenient if you just have a short amount of time and want to do a quick section somewhere. Also, the edger tool is a lifesaver. It can be done, but definitely take it one room at a time! Good luck.

@Mrs. Oreo: If you have tight spaces, make sure you have a threaded pole it can be attached to. I think it's the same you'd probably use for rolling ceilings.