Generally my approach is street tuning.  Assuming the vehicle has an existing drivable tune, I start by recording performance data, make appropriate (and conservative) changes to the tune, and repeating until having found the best solution.  If starting on a vehicle without an existing drivable tune I'll craft a tune from a similar powertrain and tune from there as above.

 

I don't rule out tuning on a dyno, but given how time consuming it can be to do a full operating parameter tune and the cost of dyno time being what it is, I find I can do a pretty good job on the street.  Of course when tuning a vehicle with a ridiculous amount of power for a street vehicle it can rather challenging to safely exercise the vehicle across all operating parameters except on a dyno.  If a customer's primary interest is wide open throttle performance tuning on a dyno can be rather cost effective.

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For my own vehicles dyno time is used for wide open throttle spark advance tweaks and getting performance numbers and baselines.

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My street tuning tools are HPTuners interface and their Scanner software, Innovative Motors Sports LC-2 wideband O2 sensor (generally in the tailpipe or optionally in an existing O2 sensor exhaust bung), and a G-tech Performance accelerometer.