Off center (not bent!) stylus?

@thom_at_galibier_design thanks so much for the detailed response that really helped me understand better. The stylus looks intact to me but I am only using a handheld jewelry magnifying glass (I think 40x). In order to really see damage you need something like 100x+ right?

In my further testing with this needle I have started to notice that it seems like it will sometimes fail to settle properly in the groove. In one very severe case I placed the needle in a middle track of a record and practically nothing but muffled thumps came out of the left channel while the right channel seemed fine. This problem was rectified by just raising the needle and dropping it again in the same place.

Does this make sense to folks as a problem that would be caused by this angled cantilever? That it can sometimes fail to catch a groove but once it catches sounds normal?

To the general question of why I am bothering with working through these issues rather than just buying brand new stuff... it's interesting and fun to me! I don't want to simply know that something is damaged I want to know why and how that affects playback.

So all your input is super helpful and maybe I will eventually be convinced to ditch vintage and go new. Or maybe not - who knows. But please feel free to keep firing away as all this is new to me and just helps fill in my (many many many) gaps of understanding.

Keep in mind that those needle drops may leave a click in the record (even when the stylus/cantilever is fine, that's a risk, unless you are dead-eye on the space between tracks). Thom/Galibier explained the issue very clearly in terms of the skew of the motor assembly; his point re the condition of the stylus itself is a good one. The angled cantilever is a little like having a misaligned drive shaft between your motor and the differential/wheels. If it isn't straight on, when running the road (grooves) it isn't going to behave smoothly. And could result in mistracking and explain why you lost signal in one channel. 
It's all good to experiment and have fun but I'd be cautious about damaging your records. I also don't know anything about the quality of replacement stylus assemblies, such as those sold by 3d parties. @chakster would be your man among others on that question. Good luck!

@whart got it thanks for that. So do you always play your records from the first track only?

@hauie88--Nope. Back in the day, I often only listened to a selected track or two from an album, then flipped to something else. I was pretty careful to drop in the dead space between tracks, but I'm human and that's an imperfect process. 
These days I do tend to listen to full sides, particularly since a lot of what I've been listening to is '70s spiritual or soul jazz and some of the tracks can take up a whole side. I will still, on occasion, do a needle drop of single track though. (I've become less dogmatic about a lot of things in my dotage). 
My concern was exacerbated by the problem(s) with your cartridge--not just aiming, but the potential for mistracking and needle dropping with a skewed cantilever could make matters worse in terms of damage to the record. 

the skewed cantilever will not significantly increase record wear but the azimuth error sure will. The diamond is pointed in the wrong direction!!
I explained the damage this will cause above. The cartridge will sound fine with a replacement stylus. So, go here https://www.lpgear.com/ and see if they have a replacement for it. Check out the cost and tell us what you find.