This is how I feel. If a payment-for-some-posting-privileges is going to happen, it couldn’t be that much harder to re-implement something very like the old membership system alongside free guest posting with ads.
Which isn’t to say that a new forum with extra-special-paid-membership on top of the old ones is a bad idea, I just don’t think it would bring in the most bucks.
Ditto for donations and swag. All are reasonable - again, there isn’t a downside to trying to sell merch through instant-inventory places. But just doing the math it seems like the percentage of people who would pay twice as much to post in one special forum, or the percentage of people who would similarly buy a $30 piece of memorabilia once a year, is just not going to compare to the people who just continue their modestly-priced membership.
All of these can help, though, and won’t hurt.
With regards to the column per se, there’s still a space in the world for a snarky know-it-all. For a while I had high hopes for What If by Randall of XKCD, but then he moved that particular column to the paywalled NYT without even mentioning it, just radio silence for years until I found it out randomly, and I’m not going to subscribe just to see if his well has run dry yet and I sort of resent him just stopping writing with no explanation.
But the fact that I would still read What If if it were still on the XKCD website shows that I for one still have a desire for a regular feature of facts mixed with humor.