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I would spend the extra money on sotf myself. At the very least it saves you from having to switch tunes and go thorough the transmission relearn process again. I like being able to turn it up to high on a long trip and get the best mileage, then turn it down in 2 seconds to tow, no trans relearn required. For the minor extra cost it was worth it to me. I mounted the switch where the power port was next to the exhaust brake button, looks like it came from the factory it is so clean. On that note thou, I'm pretty sure you can get sotf with certain tunes on sct as well, pretty sure tyrant is one of them. I would call and talk to the boys at no limit, they usually have all the options and are very helpful.
The inherent problem I've noticed with shift on the fly is as you de-tune or turn it up, sometimes the transmission shifts really weird and you're better off doing a relearn anyway, or leaving the tune in the position it was in. Learned this on my 2014, may not be as noticeable on some of the newer tunes/tuners. Mine has custom MCC tuning that was done by Morgan Primm from Midwest Diesel and Auto, has a Barder 6670R turbo, has a stroker CP3 along with a 2015 CP4.2 and 30% injectors, so it may not be the best one to judge this off of. However I am not the only one I know that's had this issue.
Sounds like a fun truck. Yeah I'm not sure about all sotf tuning I guess. I'm running patriot ndash on a 15. Seems to always shift good in every tune, slightly firmer than stock, once the learning stage was done. Unfortunately they are no longer around and I haven't tried any others, always heard good things about tyrant thou.