Clearly missing the point. The OP mentions DOS, so this was the mid-90s. OpenBSD didn't exist (Theo hadn't burned all his bridges with NetBSD yet). There were NO updates. You bought software, games especially, in a shrink wrapped box at a brick and mortar store. Most people outside universities did not have internet access. If you were an extremely privileged few, you could download small patches from a BBS or online service but this was extremely rare. You got what you got. The development model was different. It had to work under any circumstances. There was no "we'll fix it in the next sprint!" and push it to the app store. Developers had no way to contact their customers.

Regarding that hobbyist OS OpenBSD, where the developers care about nothing besides security, there were no proprietary application packages available. Most retailed applications in those days ran on SunOS/Solaris or HP/UX.