So yeah my article is relevant here and of course I'd highly recommend reading it.
My thoughts: So this is a Goons board...
The objective is to play as many Goons as possible; you've got Plaza to give you actions, and Hunting Party to help you draw cards, so you're aiming for multi-Goons turns. Note that these components will probably be contested so winning these splits could be important.
Jack is amazing for helping you with all of these things. You need to hit $6 early and often and Jack is great for that, even if you've been hit by a Goons.
Let's go over what Jack isn't amazing for here:
-Decreasing your deck size: Jack doesn't do this, and thinning is HWinning, so you're going to need a Lookout or two here. It's not super-SUPER-duper important because Hunting Party will help you out there, so it's just super-duper important.
-Drawing cards: what? Well yeah Jack does draw cards and it's especially great for drawing you out of a Goons-ed hand, but Jack is draw-up-to-5, and there are two problems with that. First, draw-up-to-X is pretty good but the lower X gets, the worse it is. 5 is not that great for building your whole deck around, so you need another source of draw. Second, decks that use draw-up-to-X as their only source of draw tend to only function well when they're very thin. This means you need strong trashing to make them happen and then they don't green very well. While you don't need green cards here (see above meme), Jack gives you a Silver every time you play it, which these kinds of decks almost never want to have. So while Jack is OK for drawing cards, it's going to stop being useful for that very quickly and you'll want to feed him to your Lookout before too long.
Certain types of engines want Silvers because that's the payload of the engine, others don't. It's easy to talk about Silver being good because once you understand Big Money you can see the value of it. Understanding Goons is much more difficult and complex, especially on boards like this where the path forward isn't super clear. You want some Silvers early but you want to regulate how many you get vs. other things that help you play Goons more.
On a 4/3 here I'd struggle between opening Jack/Lookout and Jack/Silver. I'd probably land on Jack/Lookout. On 5/2, Haggler/nothing is pretty clear.