Everyone is gonna have a different opinion on this one. Im not "rich", yet im gonna put a 5.7 in my 64 dart convertible. Why? A few reasons, one is power for its size, the other is gas milage, guess another is easy start ups and so on. As far as a stroked la block vs the new hemis, ill say this, by the time you get a good old 360 or 340 putting out even 360hp, you most probably have a lopy cam and your eninge is probably getting into the "raced on the weekends" catagory. A base model 5.7 hemi gets those numbers without the eninge being worked over at all. That said, dollar for dollar, right now it is easier and cheaper to put an old 360 in an old car, but thats because of the EFI stuff (if your gonna use it). If your gonna put EFI on a 360, itll run ya some money though, so you should just go with a 5.7 hemi to begin with. I think its unfair to compare a stock 5.7 hemi against a stroked 360. Why? I think a better comparrison would be a stock 360 vs a stock 5.7 hemi. As time passes hemi swaps will get more common and cheaper, and a stroked new hemi will out power a stroked 360 easy. Also carbed hemis are on the rise.
As far as putting a 440 in a dart...yes a stock 440 out powers a stock 345 hemi (5.7), but not by much horsepower. The big block has way more torque of corse which is i guess good for luanches and pulling tree stumps. im not building a drag car though, i want my car to handle well in corners so having a big heavy big block kinda steals my little 64 darts nimbleness away. Alot of guys dont know it, but the new hemis weigh less then la small blocks, and only weigh a little more then my old slant six (10lbs). So my slant six to 5.7 hemi swap hasnt added much wieght to my front end. Im also using the alterktion up front, so that lightens things up even more.
As far as buying an already done car, i think buying a car done already steals away the fun you have putting it together, so id feel odd buying a car that didnt have a little work done by myself, but that said if your trying to figure out prices, do the math. Add up your materials and labour and see what it comes out to. Some old cars will need more work then others. Are you restoring the cars, or just offering to do the new hemi swap? If your taking a prefectly good conditioned dart and doing just the hemi swap, id say 2o-25k sounds right, if your using new engines and trans. if your gonna be using pulled engines, id say less. If your doing body work and all that, id say more, because some cars will need more work then others.