The Wisdom will get you a nice big, easy-to-read display with air integration. Both the Insight and the Wisdom are really easy to use, this was a very important factor for me when deciding on the Wisdom years ago, and it still applies - you don't want to have to think about how you're using your computer underwater, you just want it to display everything you need. If the Sherwood isn't showing you what you need on the primary display, just press the side button for the alternate display; no worries about what "mode" it's in or other nonsense. So that's still a big plus.
The log software for the Sherwoods was lacking for awhile, but they've done a good job patching it up, so just make sure you download the latest & greatest from the website before you start using it. And make sure you get the right cable for your model!
The main "downside" to the Sherwoods - and I put that in quotes, because in some ways it's also their big advantage - is that they are possibly the most liberal computers out there in terms of Remaining Dive Time calculations, and they have no "conservatism" settings to tweak that down. What that means is that it's up to you to treat that RDT display as absolutely the best case RDT, so if you're tired or feel dehydrated or been up drinking the night before or know you've been doing a series of multilevel dives, it's entirely up to YOU to be your own "conservatism" factor and surface well before the RDT on the display. Treat the Sherwood RDT display as being absolutely the best case possible, and never "push it" with a Sherwood.
Personally, for example, if I'm doing more than just two dives on a weekend, I treat the nitrogen graph on my Wisdom as if it's two bars higher than it shows. But don't worry, especially after a series of dives you'll still find yourself with longer bottom times than your friends on Suunto computers, for example.
As for the reg, purely my opinion but for about the same as the Brut you could get a ScubaPro Mk 2/R295, an "industry standard" reg that will serve you well and which you could get serviced anywhere in the world.