I know the short answer is yes before I begin, but here we go:
The Bike:

You might recognize this one from that one time some *ssh*l* left his bike outside his apartment (still indoors though) and it got stole and then he was sad and then:
Some truly amazing people from OneXOne got his bike back to him.
And that's when the loose crank arm became a problem.
I originally thought it had to do with the theft and how that whole thing went down.
Backing up a bit, in the set up above is a cheapo Eighth Inch crankset bolted to a cheapo Tange BB(vs the nicer ones that they make). Square taper BB, hex bolts.
Eventually got so bad I had to stop during rides(and I don't ride very far when I ride) to tighten. This was during the winter, so I tried loctite(blue) and blamed it on the bike being outside during the day and brought inside at night.
Fast forward to now. I've replaced the BB and crankset. Same cheap tange, now is a [less cheap] Pake crankset. And today it's as bad or worse.
Actually worse.
I’ve done a little research and kind of concluded it’s due to ill fitting BB/crankset combos. I ride brakeless [yes incredibly stupid and no I can’t justify it. At all. No good reason to be brakeless…], so I’m putting more stress on it then the average fellow, but I’m not that strong, right leg dominant, and don’t ride that hard.
So, is it as simple as spending more money on a BB/crank set? Do I have a bad frame? (as in is the BB shelf off angle causing me to put “weird” forces on the crank set)
The weird part for me is I had this same BB(the 103mm version) in my Schwinn conversion with a *gulp* Tech9 crank set and had no such issue…
I’m building up my All City [this was supposed to be my backup/drunk/bar bike, but it turned into my daily driver because I love whatever bike I happen to be riding at the time] and want to make sure I’m not just a ruiner of left crank arms.
Sugino crank set with a nicer BB.