Apparently I can't make .44 Magnum SWC ammo unless I have both the Hand Loader perk and the schematics from Jules. The skill check for Jules requires Guns 50 (which I have) and Survival 60 (which I haven't invested in at all since I'm not playing hardcoe). Is the benefit of the SWC ammo worth the investment of 40+ points for that alone?

Is it a 40 point investment?
You only need to make the check once so temporary bonuses can help. This is where comprehension is your best friend those checks you want to make but don't want to invest the points.

Take buffout +3 Endurance=+6 Survival[temporary]
Brahmin-skin[and several other wasteland outfits]+1 Endurance[while worn]+2 Survival
Four skills books is +16 Survival
Reading lads life is a +20 bonus to survival [temporary]

Wow thats +44 Survival!

A character with five endurance and five luck would have a base survival of 15.
15+44=59. One skill point investment.
With out comprehension of course the bonus drops considerably but still brings you much closer.
Oh yes Caesar's Armor if you kill him or steal it after reverse pickpocketing some better armor it will give you +5 Survival

Great thinking, thanks! I have sort of forgotten about the chems!

You also need 75 repair at the bench when crafting. I love this ammo so it is worth it for me.