OT: How to mix guitar/synth/drum machines? Guitar DI vs Amp?

[Marcus Kirby <marcusloops@gmail.com>]

I'm using a mono synth, guitar with a bunch of pedals, and some drum samples in ableton.

I have a bit to haul around, so I'm trying to minimize the amount of equipment that I have. Which leads me to....

Issue One: Guitar DI vs Amp

I have a fender bandmaster reverb that sounds amazing. It isn't feasible to carry around the amp+cab, pedals, keyboards, etc. This has led me to going DI, but alas, it sounds bad. I've considered a small 1x12 mic'ed, but then the fullness of the guitar starts to take everything over. Is there any way to get a decent sound running DI? Can I somehow run a dummy load from my amp head, then send the line out signal to my interface? What about running the output of ableton to my tube amp?

Issue Two: Analog Synth and Guitars

I use my mono synth mainly for bass sounds. I would like to get a juno at some point, but for now, I'm sampling the synth and doing poly that way. I have a hard time figuring out how extreme the eq'ing should be though. Does anyone have suggested reading material for mixing guitar and analog synths? 

Issue Three: Mixing electronic sounds and acoustic sounds

Is anyone else mixing acoustic sounds and electronic sounds? I'm having issues with the electronics sounding a bit sterile. I've even tried synthesizing my own sounds to match the guitar, but it seems to be a constant problem.