I just did my first oil change myself today, and it was easy. No problems like the OP described.
Mine is a '12 1.4L so it has the belly pan. Mine already had a notch cut in it for the drain bolt. The car was serviced a couple times by the dealer, is there a chance they cut it themselves? Or maybe it came with the notch in it? In any case it was perfect, no oil spilled on the belly pan and it all flowed into the catch pan. And to relieve vacuum and let it drain I popped the dipstick instead of the oil filler. IMO a better option, since with the filler open its possible things can drop in there.
Jacking the car up....you don't have to jack it all the way and put 2 jackstands to do oil. For me I just jacked it on the drivers side jack point and put 1 jackstand by where the driver's front a-arm attaches. Nice and firm jacking points, and minimal effort.
Oil filter....I'm not spending $20 on a 24mm socket just to do oil. Vice grips worked well and didn't tear up the nut on top. Its not perfectly brand new looking like it was, but I don't mind. I also didn't change out the gasket, it was in perfect condition and didn't want to budge. I've leak-tested and its fine. I also didn't clean out the filter housing...seems like a bad idea, you don't want to introduce foreign particles to the oil. Better to just put up with a little residual dirty oil.
Overall it was one of the easiest oil changes I've ever done. Jack on 1 side, put in jackstand, drain oil, replace filter while oil drains, put drain bolt back in, fill it and leak test. The MR2 Turbo I had, the oil filter only had an inch of clearance from the turbo itself. You'd get 3rd degree burns trying to take it off, and it was in an awkward position where you couldn't get a grip on it. Only a specific type of filter wrench would work on it, complete PITA. Being so close to the turbo would also subject it to intense heat, enough to cook the gasket so you were lucky to even get the filter off each time. The Sonic is a walk in the park by comparison.
