Well, my Westfield has never seen a rolling road. Started off up the road with no map at all and within 30 miles on the road I had it running pretty much perfectly.
Mapping on a rolling road has advantages in that you can hold high speed/load combinations until the engine melts, but mapping on the road gives you the transients that happen in real driving that you can't reproduce easily on the rollers and yes, the engine operating conditions will always be slightly different. That should be compensated by intake air and coolant temperature sensors but, IME, you're often mapping out deficiencies in these too.
IMHO, you can't map a car on the rolling road without at least driving it a few miles to check if it's a dog to drive and iron out the little flat spots and hesitancies. Vice versa, you aren't going to wring every last few horsepower out of it without a rolling road, especially where it comes to tweaking the ignition map where the changes are subtle and difficult to detect with a seat-of-pants dyno.
Having said that, I could have spent a couple of hundred quid getting mine setup and would have been none the wiser as to how it was done. As it is, I spent that money on building a wideband lambda controller and I'm now equipped to tweak it whenever required, and have gained an awful lot of knowledge doing so. Depends whether your desire is for a turn-key working car or to learn and do it yourself.
A wideband lambda sensor is totally essential if you're contemplating this, one you trust to tell you the truth, too, especially with forced induction because it's so easy wreck an engine if it goes lean.
I find you can get the basic map dialled in by watching the lambda sensor and tweaking the map on the fly (helps if someone else is driving, but I didn't have that luxury
). More detailed tuning is best done by processing a data log that includes varied driving. I had a script that processed a datalog into a percentage error for each cell of the map, and then applied it. A couple of iterations of that and you've basically got a car that's indistinguishable from one that's had a half day on the rolling road.
It doesn't really matter if you can't hold it at peak RPM at WOT with this method. As long as you've done it for long enough for the lambda sensor to settle you have the information you need in the log.
I'm not familiar with your engine management. Most of my experience is with the various incarnations of Megasquirt.
Whilst they are all basically the same, one thing you need to be able to do is find your way around the mapping software to make real-time adjustments, so, if you can, find someone who's familiar with your system.