I understand your logic on tuning, especially coming from the "tuner" community before getting into cruisers. A wideband is a great bit of insurance, as you mentioned, you will be able to monitor AFR's in changing conditions when traveling (elevation, gas grade availability, etc.).
My point here being: I doubt adjustments to timing would be necessary for a TRD Supercharger, even with the smaller pulley. A method of tuning for additional insurance could come in the form of an air flow converter. On non-vvti SR20's (2.0 turbo) I have made reliable 350-400whp tuning on an Apexi SAFC (1, 2 or NEO) and pump gas. SAFC's are cheap ($150-250), easy to find (craigslist), and can effectively produce greater power with an even safer tune, especially with a dyno. You retain your factory ECU and wire in the SAFC to piggyback. I'm sure the factory OBDII ECU does fine trimming fuel on it's own and adapting to changing conditions/constant strain, but an SAFC could be an excellent option for those who might be a bit obsessive, on a budget.
Now if you want to play with timing and are looking for greater power, out of a more complicated forced induction setup and wish to adjust timing, AEM standalone is the route I would go. Expect to shell out $1500 + in that case though.
MUD needs a boost FAQ and/or sub-fourm.