My rant about this topic falls somewhat in line with yours: The Hugh Hathcocks require billionaires who play with money in a nearly embarrassing way (it's one thing to love a football program, but when a couple million could fund some other project you deeply care about versus paying a kid who just might beat up his girlfriend at some point is tough to swallow). So, I don't see the president box gang as the most likely big dollar funders of NIL. But, the Gator Collective is also missing the mark by aiming to be so inclusive as to miss who will actually pay.
UF has hundreds of Bull Gator boosters at far lower levels and others who would but can't make games. Instead of the $5-10 investments per month, a functioning UF collective could likely get $5-10 thousand per donor from a couple thousand people. Even the president box couple hundred would likely contribute $10-15k per year (not the larger portion but some). 500 people at $10k is $5 million per year and that investment level can be duplicated year over year. Another 1000 at $5k and we are at $10 million total, before we account for what could be the $25-50 per month group of several thousands. These are not crazy or overly hopeful figures.
Instead, GC has plotted their own ineptness by the limited ask of $5-10 per month. Add to that the structural issues I've noted prior, and won't repeat, but that lead to no oversight/"collective" input into the dollar allocation, so you really cannot get those $5-10k+ donors because they don't trust you.