Not necessarily. It depends on how good you are - or think you are - in the first place. If you're a back-end-of-the-Top 25 team, beating a Top 5 team is a great win but you are a lot closer to them than you would be a hasn't-beaten-a-B1G-team-in-three-years team so the "absolute value" would skewed the other way. If you're a 5-7 team, you're probably right.
Generally agree with this and what StPaulHusker has been saying. If it's one loss but you still win a conference championship and/or get a Playoff invite, I'm sure that's right. But if it's the difference between a 9/10 win season, that changes how much the victory is worth.
Additionally, that game for tOSU was probably quite an outlier. They had a new QB starting his second game after losing their starter in fall camp who completed less than a third of his passes and threw three interceptions. Plus, the degree of who you "shouldn't" lose to varies a lot. VaTech wasn't good but they were 7-6 and beat another Top 25 team that year. There's a difference between that and teams that haven't won a conference game in three years.
Almost everyone in the Top 25 loses a game to someone they "shouldn't" each year. I bet if you went back just two years, basically everyone has lost a game they "shouldn't". Losing to a team that's .500 or just better is probably going to happen every year or two to just about every team other than the elite. But losing to 2/3 win teams rarely happens to teams that are legitimate conference/national title contenders.