Lots of world-class tone can be had without a tube, dude. Tube voodoo is like wood voodoo... if the neo-mystic powers of a tube make you feel better, that's all well and good; however, you can get great tone without one and sucky tone WITH one. The J-Station is considered one of the most natural-sounding of the digital processors, and something like the Tech21 SansAmp is solid-state and yet full of awesome character.
Regarding the thread topic, though-- pedal boards scare me. If you think an amp modeler robs a signal chain of tone, imagine running your signal through 10 pedals? Your SNR will be just horrible.
That said, let me address a few of your specific concerns: regarding compressor placement, you should almost always put your compressor right at the beginning of the chain. Although this isn't strictly accurate, think of it as a pedal that makes your quiet parts loud and your loud parts quieter. The dynamics get all squished, which is sometimes a good thing. Why at the beginning, then? After your signal has gone through distortion pedals and the like, it will already be naturally compressed. Your compressor isn't doing anything particularly useful if you put it at the end. Furthermore, effects like phasers, flangers, and tremolo will contribute to nasty-sounding artifacts in the signal chain as the compressor tries to level their signals out. Even worse, any residual hiss (and with stompboxes, believe me there will be hiss) will be accentuated and amplified by a compressor if you put it after a bunch of effects.
On the other hand, if you put it first, it's as though only your 'clean' playing is affected. Only the purest form of the signal is being 'levelled out', at which point in time the other effects can begin to work their magic on it.
Now, I say "almost always" because happy accidents happen all the time, and compressing a flanger could produce an unexpected effect that ends up being exactly what you want!
I personally WOULD consider an EQ pedal. There's far more magic in knowing how to change EQ settings than there is in buying multiple distortion pedals. OK, so if you're happy with the one tone you get from your amp, you don't need one. But if you want to alternate between 2 tones, the EQ pedal is your friend. Even if you set all the faders at below unity, you get a reduction in signal which might 'clean up' your amp. Or, if you set a mid boost, it might drive your amp in a way that it wouldn't otherwise drive it. It's probably the most versatile and underrated pedal out there, but it's a real secret weapon that'll change your approach to the way your amp and guitar interact.
Greg