I have driven several of each of these, 4430's, 4440's, 1066, and 1 1086 helping 1 farmer or another over the years. The 4430's I would say was the weakest of the bunch and did start poor in the winter. Seems that was what all 30 series were known for. The 4440's as you say would run rings around a 1066 or 86 and have power to spare. Didn't seem to matter if it was a quad or a powershift model. Other than the 30 series Deere, I have never had another make, be it IH, Cat, Cummins start in the winter as well as the Deeres.
The 4430's had a turbo-ed 404 cu in engine. The 404 was stretched to it's practical limits and as a result used a lot of fuel and sacrificed reliability to squeeze 125 hp out of it. I know of a few that were turned up to 135/140hp and didn't hold up at all. The smaller 30 series weren't bad starters...the 4230 and 4030....The 4430 and 4630 were different stories, albiet a MUCH more "user friendly" tractor just because of that cab!
The 4440 had the 466 cu in w/turbo. It was tuned quite mildly to get 130hp. I've seen many a 4440 tuned up to 155/160hp and as reliable as death and taxes. The same engine (w/ an intercooler) put out 200+hp (pto) on 4960's before the 4000 series was done. Deere sent IH back to the drawing board with the 4020, and the 4440 was the coup de grace.
I always wanted a 1066 IH. Even the Binder faithful will tell you the 1066 was a better tractor than the 1086 when all is said and done. I found a mint '74 open station model about a year and a half back. I was quite disappointed with it. It dynoed 145hp, but just didn't have what it takes under a load. It had the noisiest tranny I've ever been around, plus it shifted like it had cement in the gear box. And...as is USUALLY the case, the T/A was starting to go south....
Then I found the 4440. '81 model, Low hours, Power Shift, new radial duals, new cab kit, full weights, quick coupler, and 155hp on the dyno. (I've since dialed it back to 140hp) It is a joy to run and a horse of a tractor. I've put it on a 15' bat wing for a couple days, but mostly it's used to pull an 8-row planter or a 15' no till soy bean drill. Gonna try it out on a 650 bu grain cart in a few weeks. I did try it out in front of the 20' IH 496 disk. She let the black smoke roll, and handled it like a charm!
I tend to like ALL brands. No real favorite. But I do like certain models within all the brands. The 4440 is hands down one of the best models EVER from ANY brand. Where I live, Massey Ferguson owned the market for smaller tractors and IH held the advantage on 80hp and up tractors until the mid 70's. By the time the 40 series Deere made the show, it was all over for the red guys....Our IH dealer shut the doors in the early 70's. They saw the writing on the wall.....Big tractor and combine market here now is probably 75% or better "green".