There are no m39 (Jupiter 3) to Canon - M focal reducers AFAIK. In crop, you will get rid of the outer projection circle which usually has the most pronounced aberration effect. Jupiter 9 should be fine. (non-intended rhyme)
m39 can be converted onto Canon EF correctly though right?
No

M39 can not be converted (without corrective optics) to Canon EF but it can to Canon EF-M.
There isn’t focal reducer for the most of m39 (rangefinder) lenses.
Focal reducers works well for any SLR lenses when adapted to APS-C and smaller sensors.
Existing focal reducers can’t be used on full frame sensors (unless you don’t use medium format lenses and find someone to design such a focal reducer. Maybe there are some already, I don’t know.)
I have a 5d4, and a Viltrox speedbooster EF -> EF-M. This makes the m50 practically a full frame camera (with quality loss obvs).
Yes, that works well and with the high quality FR such as Metabones, the image quality can be actually improved a bit in the major projection area.
The question is why using EF lens with FR on APS-C sensor when you have Canon 5D IV, if not for the smaller setup? Otherwise it doesn’t make much sense.
The difference is about 10%, so probably a light vignette around the edges?
No on APS-C. The image has a slightly narrower FOV so the vignetting should be similar as on a FF.
Were these two images taken on a reversed Helios? I love the portrait shot.
I have a 44-2 and a 44-4, the 44-2 gives flare and haze and glow, which makes it interesting. The 44-4 is a competent, sharp portrait lens.
But I've got loads of competent portrait lenses! So it's gonna get modified!
I'm in the same boat, which is the whole point of this thread, I've gotten awesome Canon glass to shoot with, its about looking for something different\something unique. Earn with the Canon glass and shoot this stuff for fun!
Was it a 44-4 or a 44-2? (or does it not matter)
It was 44-2 but it should not matter much.
Cool. They look awesome. Gonna have a go at that when I get a minute.
In a resume:
M39 lenses (rangefinder ones) can’t be adapted on a Canon EF (DSLR) but only on mirrorless cameras. (FF and smaller sensors, such as your EF-M)
You can’t use focal reducer with these lenses on any camera
There are a few m39 lenses, such as early Helios 40 e.g. that have m39 mount but they were design for the M42 flange distance and can be used on some DSLRs as well as with the focal reducer with a simple ring m39 to M42 adapter.
There is no real benefit apart of the size to use lenses with focal reducer on a APS-C or MFT camera if you have a native mount full frame DSLR for the same lenses (unless there is a big difference in resolution or noise).
Some lenses such as Canon FD, Minolta (MD-A mount and a few others) can’t be easily addapted on your Canon 5DIV, but can on your M50 with or without focal reducer.
Give your Helios 44 a try with the flipped rear element. You can aleays put it back.
Hope it helps,
Viktor