Need help deciding what to buy!

I am asking all you gear heads for some advice. First I'll tell you what I want to do, then give you my background, budget, etc.

1. I want to be able to create lots of fun sounds and effects with my guitar, for fun and for recording. I would like not only amp modeling, but synth effects if possible. I would also like it if I could use the gear as a practice aid, meaning that I could lay down riffs or bass lines that I could practice alongside of (loops?).

2. I'm 43 years old and have been playing guitar for about 30 years. Most of my play has been acoustic rhythm, and I've studied some nylon string classical. I own a Martin D-16, an old Yamaha classical, and a few years ago bought my first electric, a used Zion custom strat (2 single coils, one humbucker, Kahler tremolo bridge). I only own one amp, a nice Roland keyboard amp. Both of the acoustic guitars have had acoustic pickups installed.

3. When I was younger I played acoustic rhythm guitar for singing groups, and about 8 years ago I gigged a little bit for a professional guitarist who needed someone who could play a little and sing. We did "two man band" using drum tracks, effects, etc., but the other guy did all the thinking and arranging, I just strummed and sang.

4. The longterm goal would be to have fun recording and maybe perform a little if I have time.

5. My budget is very flexible; I'd spend 1-2k or more if necessary. I'd buy whatever effects units, guitar modifications, or even a new guitar if needed.

6. I've looked at the Roland VG99 guitar synth, but don't know if I need a special pickup to use this, and if it's optional, I wonder what the difference is with and without the special pickup. I also don't know if I need something different for recording, or if I can just do that with a USB cable to a computer.

Thanks for any help you guys can give.

86general
Green Brook, NJ