As with anything, you're going to get tons of different opinions on these things. Here is my opinion on things as a session guitarist and teacher:
Electric guitar and acoustic guitar may share tuning and fingerings, but in some ways they are actually different instruments. Being good on one doesn't automatically make you as good at the other. Acoustic players have fretting-hand strength many electric guitarists don't need to have, at the same time electric players often have fretting-hand control (bending, vibrato, muting at distorted amp settings) that many acoustic guitarists don't need to have. Players who are good on both generally have had to practise on both, and adapt their technique accordingly depending on which they are playing.
A great starter amp, IMO, is the Roland Micro Cube. It is probably my favourite amp of the six or seven that I own and gets the most play time by far. Inexpensive, lightweight, has several great-sounding amp models, decent effects, easily more than loud enough for practice or jamming with an acoustic guitar, and even works off batteries.
Bass guitar is a completely different instrument, but well worth studying for any serious student of the guitar. Again, being good at guitar is no guarantee of being good at bass and vice versa... but if you are a guitarist, getting good at bass will inform your guitar playing, and vice versa.
If you want to learn to set up your guitar, get the book by Dan Erlewine and save yourself a lot of time. He is the man when it comes to these things. Having said that, I have learned to do pretty much all setup duties myself, but still send my main guitars to a trustworthy tech to do it properly. I need to know my stuff will play impeccably and won't fail me in front of 10,000 people... perhaps your situation is less urgent, but I still think everyone should have their favourite guitars tweaked properly by a professional at least once so they know how good it can be.
RE the topic of Squiers, it really depends which you get. The older Japanese made Squiers are highly sought after, especially the ones from the early 80s which were arguably superior to the US-made ones of the time. As long as you avoid the Chinese / Korean-made Squiers you will probably do all right, but in that price range it is definitely possible to get a better guitar for less money if it doesn't carry the Fender name.
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