Since I got my '41 I've wanted to upgrade the powerplant, either with a 235 Six or a 283 V-8; however, I have the opportunity to purchase a '58 Buick 364 nailhead and transmission for cheap. I love the idea of an alternate to a Bowtie engine, though I know this particular swap would require a helluva lot more effort than just bolting in a 235. Anyone ever attempted a similar swap?
I would go with the Nailhead and get the frame adapters from Chassis Engineering. Easy to use, no welding, bolt on. You just need to make sure you have enough room between the radiator and firewall.
Stick or auto? if it's an auto, it's a Dynaflow trans. 364 is a cool choice, but a 64-66 nailhead with a 400 is a better way to go.
It's a Dynaflow, and while I like your idea of a later-model motor and tranny, my Ultimate Goal is to try and keep whatever I do to this car as 'late-50's period correct' as possible. Though I'm sure I will end up bending that rule many times before it's over.
Because the Dynaflow is set-up for a Buick-style torque-tube your are going to have to do something different for a transmission - I don't think anybody ever modified a Dynaflow to fit the Chevy torque-tube nor modified the Dynaflow for an open driveshaft. In the 'old days' you could find adapters for Buick to early Chevy standard transmissions but they would be hard to find today and the stock Chevy 3-speed did not tend to live too long behind the Buick. Best bet would be to adapt the Buick to a late-model GM automatic and put an open driveshaft in the Chevy - I believe those adapters are available. The nailhead would be nice in a Chevy coupe - hope you can find a way to do it!
I like the nailhead idea. But i wouldn't use the trans. If you want it to be a period correct build, don't tell anybody you put a newer trans in. Unless you run over somebody and they are under your car. .. no way to tell.
Centerville Auto Parts has the adapter to put any Chevrolet transmission behind that engine. If you use a stick transmission you will need his adapter for the back of the crank. Call Nailhead Russ he knows everything about that engine. Here is a link to his engine swap page. http://nailheadbuick.com/nailhead-engine-swaps
I had a 283 in my '540 coupe. I did own a 364 in a '58 Roadmaster once and liked the engine real well, if the tranny is a dynaflow you are probably not going to like it much. The engine should go in no problem, you may have exhaust issues but those can be over come. Any number of transmissions can be adapted to the engine too so you are good all around.
LOL there was a '36 Chevy truck for sale here that had a 302 and c4 in it. Seems backward but when you get right down to it if you can put an SBC in a Deuce why couldn't you put an SBF on a Chevy. I like the nailhead option for the 41 Chebby, probably not the first thing I would think about but it is a good swap.