jastrub

I prefer earphones because there is less chance of feedback. However, I do kind of want to get either an analog amp-to-mic rig or an amp simulator, so that I can get better guitar tones. Any suggestions?

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Freebase Dali

You shouldn't be using monitors when recording/tracking in the same room. Your monitors are for mixing what you've already recorded, so you won't have to worry about feedback. Headphones are what you'd use while recording simply to also be able to hear the tracks you're recording along to. They don't have to be great quality, but you definitely want them to be closed so that they provide enough isolation for your purposes.

As far as VST amp simulators, two good ones that I use are Guitar Rig 3, and Amplitube 3. Both are completely capable of producing convincing tones right out of the box, and allow for as much customization as you'd ever need.
Then of course you can also use an amp modeling pedal like the Digitech RP500 or a ton of others. I only have experience with the Digitech, but it allows you to select a bunch of different models for cab, head, mic, amp, etc., and you actually get the tactile control one might require. Personally, I don't require it as I don't perform, so it just collects dust and I use my VSTs instead, because they're far more customizable and easier to integrate with my recording program and its own features.

If I were you, you can't really lose by at least trying out some VST sims. But you need a pretty decent amount of RAM and a decent audio card if you expect to get manageable latencies when plugging into your computer DI from guitar. Of course, that's easy to skirt if you're ok with recording straight DI tones without any sim on them during the recording. If you can do that, you hardly need much else. But that's not as fun...