1) Until a couple of years ago, I lived in Huntley IL. Not exactly next door but in the 'neighborhood'. I do miss the IL area but I really lile my GA taxes!
2) Complicated...The good news, when learning the guitar, you will always be learning with guitar. The better news is; you don't need to learn it all now. I've been teaching my wife and she felt the same until I broke it down a little. The Guitar Tricks program helps with that a lot by walking you slowly in to playing. I told my wife that if you know the 'Cowboy' (open) chords and the pentatonic scale, you can play 75% of most songs on the radio. I would not quote my actual percentage though. The point being is that it seems overwhelming until you start making the small, first steps. If uyou start with bebop jazz, that's complicated but I assume you're not trying to tackle to tough stuff first. The meat and potatos of playing are not that scary.
3) Failures...Sure, when you feel commitment waning, failure may happen. You seem to keep trying. So I think you really are motivated to play but the right pathway to success has not been available to you. Hopefully Guitar Tricks will do that. Coming here and asking people of all skills about points of frustration, it helps. You have people exactly where your at, a few steps down the road, experienced (like me) and the best part; instructors like Chris are often answering stuff.
4) The 'Elaine effect...Well, true. Set a realistic expectation. Let's say you're right handed and you decide you want to throw a ball left handed. Do you think you will be able to throw lefty as well as with the right immediately? Nope. You wouldn't expect that and would know that you'd need to practice that skill. Guitar playing is a new skill to you.
Don't watch an expert (instructor) feeling dejected. They're the expert. I watch a legendary guitar player and say 'man, I sooo cannot do that'. However, they're a pro and I'm not and they spent their life getting better. I've become a solid player from years of doing it but no one's callin' be a legend. Adjust your mental viewfinder accordingly. At first you're gonna stumble but take your small victories as victories. Those small victories at the beginning are everything.
4) Forums...I kniow I mented above but it's a good place to get help. It's an intenet phone-a-friend. Document progress too. There aren't a million people on the boards but the regular group of varying level are pretty useful when you need it.
Lastly, best of luck and you can do it.