Having been a guy who started off with a lesser product on a lot of things and later regretting it, I'm not sure of the difference in prices you're comparing. Ultimately, price does make it a bit more personal. I'll share a saying:
"A cheap man always pays twice."
I've bought the lesser item and wound up frustrated, only to shell out a lot more to "make it" what I wanted. Finally, I wound up frustrated and I spent almost as much getting the lesser item to be acceptable (or even higher price) than the other one. Talk about buyer's remorse!
So, just offering a few thoughts... I don't know your personal situation, but if the shipping is $150 for the one, but the upgrades are big for the other, might it seem a bit like these cancel each other out? Then I'd look at the straight-up MSRP and then watch for sales.
My smoker is on its way, an Old Country Wrangler. I set a requirement for myself, it'd be big enough for personal use, but I have no aspirations to go pro. So size was less important than quality (I've had cheap, and it was OKAY, but I won't go that route again). I picked what I did based on thick steel, sturdy construction, and ensuring I'd have the best bang for the buck as a foundation for the things I can't simply add on later. That was my decision point, and definitely, YMMV.
I've read great reviews about the older OKJoes, but the newer ones were said somewhere to be cheap Chinese knockoffs with the name. Positive reviews of the newer ones tended to be while the unit was still new and the "new toy lustre" hadn't worn off yet. I intentionally shied away because I had some "must have" features in mind, such as thick steel construction with good welds, and the OKJoes seemed to have gone with thinner steel. Features, schmeatures... I'll add on as I go.
It's a balancing act, and I'm sure that you'll decide what you need and go from there. And I'm sure you'll enjoy what you get, but will want to modify it to make it better (I think that's all part of the love for what we do that makes us do this!). And believe me... NEITHER choice will be WRONG. It's not like you're getting married to it and hoping you don't file for divorce right after the honeymoon! :)