Hi! I'm William (Bill) Claytor, Senior Software / Quality Engineer with 25+ years of experience transforming manual QA into scalable automated systems, currently working on AI-assisted Dev/QA workflows.
Setup is a huge factor. I got a $300 parts "Telecaster" on Craigslist and took it to Bill's Music (https://www.billsmusic.com/) for their premium setup and it definitely took it to the next level in terms of the electronics, frets (especially worn and / or protruding), intonation, etc... So if you have a guitar you want to love that isn't quite there, consider getting a pro setup by a shop you trust.
I have been playing for 50 years at this point. I'm currently playing something similar to this (0) bought at GC for $329 and while the knobs and jack could stand to be replaced (especially if you are performing) it plays and sounds great. You do not need to spend more than $500 to get a solid electric guitar these days. You can definitely spend a lot more for a top tier brand like Fender, Gibson, PRS, Suhr, etc... but there is a lot of good value between $250 - $500.
Once you start getting into many tracks and advanced routing it seems like the choice (for me at least) is Logic Pro or Ableton Live. And I find Ableton much more fun to use when I want to jam, whereas Logic feels more like programming which is also great. FL Studio is also lots of fun. Try various options and see what fits best with what you are trying to do.
Ableton Live is very intuitive and there is a lite version that is bundled with some interfaces (https://www.ableton.com/en/products/live-lite/features/?pk_v...). It has been years so I don't remember which interface / version I started with but I quickly fell in love and upgraded to the full version. The time I have spent learning it has been fun and worthwhile, so maybe give it a try.
For my last several Amazon returns I did not have to use the original (or any) packaging, nor did I have to print a label. I did have to initiate the return through the app and take it to a UPS Store, where they took the unpackaged item, scanned the provided QR code on my phone, and gave me a receipt.