I use a loudbox mini. I like the basic sound of it. In smaller settings it is all I need (or want). It is very easily portable. I went to get one of the bigger loudboxes for more features, but oddly enough, I didn’t like their basic sound as well. Mark’s idea for starting a sound system piece-by-piece is interesting. Which ones do you like Mark? I do like the line array systems like the SA220/330s and bose systems. They are more capable for coverage and full range sound than my mini, but they are not near so easy to transport. It is a whole different animal (and the Bose and SA’s seem to target totally different strengths). If I were trying to cover a place with 100+ folks, I would probably be looking at one of those systems (of course when things get larger, we typically have a PA, so I have a hard time justifying a bigger setup).
All that said, your ears are different than mine. I suggest that you go play a bunch of systems with your equipment. While you are trying them out, don’t be bashful… crank it up a little as well as playing softer. If you sing, see how your voice sounds on it. Hopefully the right system will jump out to you as it did for me.
Just had a thought… one of guys on here (Doctor Guitar) made some line arrays that sounded like they were phenomenal. I might hit him up for some DIY guidance if you are so inclined.