Hi Gabe,
I will try to help and feel free to drop me a line. Right now, more so than when I was younger, there is a fantastic selection of guitars in the $500 and lower range that really do the job and are great quality instruments. First off, when I start looking, I establish a budget. How much do I want to/can spend? What vibe or tone am I going for? Are there artists that use a guitar brand that I love to hear on recordings? I have several guitars, much to my family's chagrin, lol. I have guitars from Paul Reed Smith (PRS), Gretsch, Epiphone, D'Angelico, Gibson, Fender, Schecter and Squier. I want to add that I've collected, purchased and traded a lot over the years!
I also recommend using reliable reviewers like Dawson's, GAK, PMTUK and Anderton's videos to see reviews and demos of gear. I, personally, find the reviews in the UK are really thorough, honest, and spot on. A hard part of this is trying to figure out what you like. If you haven't played a lot of guitars or amps, that can be daunting. If you are able to go, a music store is a great place to start. Play as many guitars and amps as you can in the budget you set to find out what sound best and feels best to your ears and hands! Epiphone, Ibanez, Squier, PRS, Schecter, Gretsch and Fender all make great guitars in a lot of ranges. I find PRS to be such high quality, even from their SE series, however their lowest priced instruments start at $495 here in the US. Jackson is good too.
Ibanez, overall, is really consistent in their QC, as is PRS, Epiphone(now especially), Schecter and LTD even. There really isn't a right or wrong answer. Just go out and play! I follow the same logic for amplifiers. A great place to start is what tone do you like? What do your favorite artists use? A huge question in the amp world is British or American tones? My favorites are Fender, Marshall, Orange and Blackstar is cool too. I had a Mesa Boogie, and like them, but I love British amps, especially Orange. Boss is making great amps that are really affordable that do practically anything. Play as many amps as you can.
I will try to wrap this up, haha...Overall, play with an open mind, ears and hands. Pick what you like, regardless of anything else. A reliable salesman will help you discover what you want, not just sell you something. If you are in the US, Sweetwater is a wonderful company to work with any purchases. A basic starting point, budget wise, is between $300-500 for a guitar in my mind. Anything cheaper is going to have quality issues in a lot of brands, but reliable ones are Ibanez, Yamaha, and Squier in the lower end, less than $300. Epiphone is making strides too. watch reviews, play and research. Take your time.
Happy Hunting! Feel free to reach out. I hope that gives you a starting point!