As you seem to know already, trial and error is the best way to learn what works with your rig, but there's nothing wrong with asking for advice on these dilemas. Some folks get worked up when people ask 'stupid' questions about pedal order, but it can be tricky, and there are so many combinations and different pedals have different quirks, so I always think of these as fun 'puzzle' threads...
Now, "What overdrive should I get?" threads ARE stupid....
In your case, I think I'd suggest trying:
Bass
Wireless
Octaver
Filter
Chorus
Compressor
Volume --> Tuner
Sansamp
Amp
I'd put the octaver first to help with tracking and I think folks seem to like octave before filter if you ever use them together, but I really don't, so I'm not the most qualified on that one. I'd put the Comp later to help with peaks caused by the octave or filter. I don't think it would matter much if the chorus was before or after the comp, but I like comp last-ish. I use my Pitch Black tuner last and it works flawlessly (in drop C), so I think the convenience for you is no problem. I'd keep the sansamp last to act as a front end to your amp.
-JV