I tie my fiberglass boat to the trailer (And drag it on) with a U-bolt bolted to the fiberglass bow. I think you're underestimating the strength of fiberglass... Jacks mount with LOTS of screws, so each one takes relatively little load. You place much more stress on the tie-downs, most likely...
On your visit, I suggest you inquire about it. If they're just using wood type screws directly into the fiberglass, that would be a little sketchy. If they've sandwiched an aluminum plate in there, so they can drill and tap, or just use self tappers, that would be better.
I'd agree with the above, that a visit to Outfitter requires you to actually seek them out and ask questions. But realize that Outfitter is a smaller outfit than hallmark.
Once you get in and ask questions, they're helpful, but you have to make the first move, or they don't exactly drop what they're doing to come and talk to you. They're all busy, generally speaking.
I got a really good rundown of the Outfitter Caribou Lite when it was new a few years ago. That's by far my favorite model, but I just couldn't justify spending $17k to replace my $2k still fully functional (24 year old) Hallmark Ute, which has pretty much the same layout. I keep hoping others will buy one, then sell it because they want something bigger... Unfortunately, I think a used Caribou Lite is going to be a tough find.