Actually, if I understood correctly, one of the two Jerry bought is a 944S2 Cab.
Having owned one myself I wholeheartedly approve!

I’m surprised it took this long; I fully expect rare model (951S, rare-optioned S2’s), low mile 944s to start bringing E30 M3 money in the next five years or so. The 944 is everything an entry-level millennial collector is looking for, and I don’t understand why there is such a massive value gap between the 944 and the 928 (which is not to say the 928 is overvalued).

It’s easier to understand why there is a significant price difference between 944s and 928s when you take into account the number of each that we’re built.
Collector car values are a function of both desirability and rarity. For a car to command high prices, both have to be present. Simply put, 928s are relatively more rare than 944s (in general). As a higher spec car to begin with they are also more desirable to most people as well. Thus the higher values we see for the rarer 928s (GTs, GTSs, and low mile originals of some years).

If we narrow your focus to more specific and rarer 944s (turbos, turbo S, special editions, S2s), we can already see 944 prices heading upward for quality cars.

On the other hand there’s nothing wrong with the more common 944 variants remaining affordable IMO because it allows many of us to own a truly awesome 80s era sports car that would be financially unattainable otherwise.

While the 928 was certainly built in fewer quantities, the 944 has basically been a disposable car for most of the last three decades. Given that, I wonder how many 944s are left vs 928s; 356s were treated in much the same way as the 944 for the vast majority of their lives, and as a result, they are now rarer than lwb, long nose 911s.

I get the performance advantage of the 928 vis-a-vis the 944, but I think the 944 is a much better-looking, less polarizing car athletically. I’m actually surprised the 928 is as desireable as it is, as I personally think they’re just so ugly. I really, really want to like them, and I appreciate the design nostalgia, but I just don’t think it’s a good-looking car. The 944, otoh, is dead sexy once you upgrade to a Euro rear bumper and adjust the stance, and doubly so for the Turbos and S2s.