I think the OP’s question was directed to LPs marketed as "audiophile" rather than the not so simple task of finding a "best pressing" among various commercial releases.
To the OP’s question, many of the direct to disc records sound fabulous-- the music itself is a question of taste.
The MoFi’s (the original ones pressed on the JVC vinyl in japan) were fabulously made and many were offered at a time when the quality of US vinyl was shoddy. In retrospect, my experience is that some of them hold up sonically, while others sound "fiddled with" compared to other, regular commercial copies. The vinyl formulation was superb, though, and in my view, has never been bettered.
At the time, most of these were more expensive than the standard issue, but not extraordinarily so. I have shelves full of them that I rarely listen to, from the old Mark Levinson and Wilsons, to various direct to disc, including M&K, Sheffield, Crystal Clear and a host of others, including a lot of the old MoFi.
I can’t comment on Tom Port- discussions of his business model usually involve controversy over the price of otherwise common pressings. The cost is in the identification of a good sounding copy. I go through this process on my own to lesser or greater degrees depending on the record and how much I care about it. That can be time consuming and costly.
There are some very well known "best" (or great) pressings -- copies that were generally released (not as "audiophile") and at the time, probably regarded as nothing special to most people. With the Death of Vinyl, and the obsessive pursuit of older, analog copies, entire communities have been built (virtually) around seeking out and comparing various pressings, identifying them by country of origin, pressing plant, deadwax nomenclature, etc.
This is different than collecting Blue Notes or other high value jazz or classical records which today command a high price.
The biggest bugaboo with old records, apart from identifying preferred pressings, is typically condition.
To the OP’s question, were these worth it at the time? I’d say yes, having bought and enjoyed many of them. I would distinguish this from the current audiophile pressings (almost always remastered reissues rather than original releases). In some cases, these current (even if out of print) audiophile releases make sense given the cost or scarcity (and condition) of the original releases. And in some cases, the audiophile remaster actually does sound better than the original commercial release (depending on what you call the "original").
I think, from today’s vantage point, looking back, you have to take it on a record by record basis, rather than declaring that an original pressing or the audiophile remaster is better. And, even in that comparison, people’s views will differ, depending on personal preference, system strengths (or weaknesses), etc.
