One way to do it is to take it 'step-by-step and back around to the beginning'.
Start with your guitar and the way you play. You'll come back again and again to this, no matter what you choose to put between you and your listeners.
Choose a preamp that sounds best to you, no matter the equipment that comes after it. Some of these have headphone outputs. Listen to just the preamp and find one you prefer.
If you want effects (compression and reverb can be nice) they come next. There are pedals and boxes of every description, some of which are part of the preamp system.
Amplification. If you are just playing solo guitar, the needs are simple. If you sing (and use condenser mics), play with others, or want a system that is more flexible. Again, some of these come 'bundled' with other elements of the signal chain and some stand apart.
Speaker(s). These come in various qualities, sizes, configurations, weights, and costs. A speaker you use for your main house may double as your monitor in a band or group situation. Some speakers have their own amps, especially these days. Again choose something you like.
For my tastes, I start with the best quality I can afford, and build my system from my guitar on out. I did skip a bit at the end and go from my preamp and mixer to the speaker. The amp I have is destined for ebay. The ones I want are much dinero. I will wait.
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