Only your remote tuner can answer that question. If he's doing it in live time, it can be done quickly. Basically, you do a reference dyno pull, send him the data. He immediately tunes it and sends it back. You flash the tune, do another pull. Repeat until done.
The problem with remote tuning is many of them (large companies mostly) will take your data and send you a tune back in a few hours, the next day... or later in the week. Most remote tuners can just use data pulls from a WOT pull out on the street. Of course, there's some LEO risk with such things as you need to do the pull to the top of 4th gear. In a Hellcat, this would be well beyond felony infraction level
The problem with remote tuning is many of them (large companies mostly) will take your data and send you a tune back in a few hours, the next day... or later in the week. Most remote tuners can just use data pulls from a WOT pull out on the street. Of course, there's some LEO risk with such things as you need to do the pull to the top of 4th gear. In a Hellcat, this would be well beyond felony infraction level