Think this is much more YouTube-guy-clickbait-opinion rather than any interest or intention of moving up with some of these programs.
Hobart is already DI in lacrosse, and I'm not sure they can play up from DIII to DI in two men's sports, given DIII offers championships in both. Regardless, I believe the NCAA rule 65-1 means they cannot offer scholarships if they were to move to DI, so a big hurdle in terms of competitiveness.
From a facilities standpoint, he's talking nonsense about the Hobart rink being nice and just needing some upgrades. The Geneva Rec Complex is basically a roof with glass walls, metal bleachers only on one side, no real facilities for fans, etc. Some pictures here:
https://hwsathletics.com/facilities/the-cooler/6
I went there last year to see Hobart v Middlebury. The coldest hockey experience I can remember other than a few games my freshman year at Middlebury in Nelson Arena, which was basically a metal shell. There's no way Hobart could go DI without a new building.