In 2008, if you had mostly LLLL.com, 4N.com, 5N.com and one or two word brandable domains then it was WORSE back then compared to holding an equivalent portfolio today. Like much worse since 4N .coms were still being sold for mid $xxx (crazy, right?).
In 2008, if you had mostly EMD domains it was MUCH better back then. 2-4 word EMD domains were a goldmine back then, many with 10,000+ search volume were still available to be registered and that domain name was almost guaranteed top 3 on Google with minimal effort. This is why they could be purchased for reg fee and resold for $xxx+, most of the time on the same day, especially on SEO forums and such.
From my personal perspective, domaining was better a decade ago as there were far more opportunities than there are now, also less competitive and more demand for domains in general. The chat room on Namepros used to be filled with people buying and selling every single day and regular auctions, and that was just the reseller market.