Welcome to THR! I hope you find the information you are looking for here!
The 238 is a good gun from all accounts. Every firearm has its little quirks about assembly and disassembly. You will learn them, and you will get used to them. And yes, you will be able to do all the required maintenance on a Sig 238.
Above all other considerations (except maybe reliability), you should get a gun that you like. If you shoot it well, a modern handgun is not going to be too complicated. A GLOCK is easier to disassemble, yes. Big whoopie ding dongs! You will not be doing disassembly in a gunfight! If you can read the directions, you can disassemble the Sig. After a little practice doing disassembly, you won't have an issue. Being able to put rounds on target reliably is a much bigger issue. If you like shooting the 238 more than the Glock, go with the 238.
The single action trigger with a safety is a practice issue. If you practice enough with it, you will be comfortable with it. Someone already mentioned that you can try carrying it cocked, safety on, no round in the chamber for a while, and when you notice that the safety doesn't get bumped off you can switch to a chambered round. Also, when you are practicing shooting, make conscious effort to make sure your trigger finger is not on the trigger. It would take both actions for it to go off when holstered, and your holster should positively keep anything from getting into the trigger, and your safety should be a (good) redundant precaution.
And, .380 is just fine. As good as .38 special. Not ideal, but no handgun is ideal. Let's get a caliber war going! NOT!
You also might want to find a .327 Ruger LCR to try out. Six shots, and you can shoot everything from .327 Federal Magnum fireball ammo to plinking ammo like .32 S&W Short (think recoil like a .22 mag). Plus, it doesn't weigh much (if any) more than your Smith! I'm currently waiting on Ruger to come out with a 3" LCRx in .327 myself. For me. My wife might like it too, but it's for me! Unless she steals it and hides it.