I think it would be cool to tune for yourself, but "time" is my reason for not learning and surely having to rely on someone for tuning when the time comes. I just figure after the headache, time, and money of modding these cars. Just sit back, give one of the reputable tuners your business, and let them do what they do well, and also do all the time instead of me being tired and spent with all the wrench turning and then having to worry about making it all "jive" together electronically.
To me, mechanical labor is far too expensive to outsource the work. I'm sure a 250 dollar gear swap could easily double or triple in cost to have someone else do it, or a 7K supercharger kit, costing 9, because you didn't do it yourself, but 400-700 dollars to an expert tuner to make all of your bolt-ons work well together sounds like money well spent.
On the other hand, I've never been above using a handheld tuner to subtract a few degrees of timing to anticipate nitrous use, or add some fuel to enable me to turn the wick up on a blower, but that's literally nothing imo.