You will definitely get more tech on a Jen Too (2017+), stock to stock, slightly better power, slightly better suspension. But... You can get a Jen Juan significantly cheaper. Unless you are a true off road hero, exploiting the Jen Too advantages over the earlier Raptors is very challenging.
I have plenty of “projects” from ‘smithing to bikes, SxS, and the Rap. Honestly, at some point it becomes a chore to keep up with ( yeah #FirstWorldProblems ) I enjoy that the Rap is capable of doing what it does and is capable of so much more and still backed by a full factory warranty.
You have to decide if the extra coin is worth the $$$. If you’re addicted to the v8 rumble, and it’s v8 or nothing, just stick with ’14 or earlier trucks. You can definitely add a blower, tune etc. but keep in mind you’re definitely exceeding the ratings of the long block and transmission and if you use it hard, you’re going to break something sooner or later.
Jen Too has similar limitations; the transmission is rated to ~590 foot pounds IIRC, so once you go beyond that, you’re pushing things. a tune on a Jen Too will easily bust 600 foot pounds. That being said, there are plenty of tuned
2017+ trucks running around on stock internals, etc. and going strong.
You can discount the as of yet, vaporware Raptor R. I’ve been saying since the first “rumblings” that it won’t make it to public sale and I’m sticking with that prediction. I think Ford is too Ch!cken$hit to attempt to take on the TRX for fear of trying and failing, taking the CAFE hit and crunching the numbers and realizing that the actual number of consumers who will follow through and buy it are maybe 5000 or so, making it a potential money loser. Now, if gas was $1.80 for super, yeah, they’d sell like hotcakes if they were sub 90k but that’s not reality.
In my world, I’d go for the Jen Too. That said, if I could score a Jen Juan under 30k... I’d take a hard look...