I'm about to buy a go devil long tail for a 14X44 G3. I have friends with similar boats running a 23 HP but I'm wondering if the 16HP would be enough or should I step up to the 23 also?

If you are putting any sort of a load in the boat, go with a 23. Are you buying a new motor? If so take a look at a Back Water Swomp 23. It's the best longtail out there. The innovations they have incorporated in their design have thrust them to the front of pack compared to other builders. They build a hell of a motor.

Yea I read up on those. They look pretty sweet. I found a pretty good deal I don't know if I can pass up on a brand new 16hp but I just want to make sure I won't be stuck with something that I won't be satisfied with. Thanks for the input.

Well, good luck. Just know that saving the extra scratch for a 23 would be worth it in the long run. Either way you'll get to where you want to be.