You touched a nerve with that one. My greatest "one that got away" regret, one that still haunts me, is the one I passed on 40 years ago as a teenager shopping for my first deer rifle. A mint condition 99A in .308 in the used gun rack of our local dealer. I can clearly recall wanting it pretty hard but getting a very lukewarm reaction from my dad, uncle and granddad, who were all bolt action guys. As in, it's your $250 (yes, that was the number on the tag) and I suppose it's OK if that's what you really want, but... I would have expected a similar reaction had I expressed an interest in applying for cosmetology school rather than college. I didn't have the guts to make a stand. I can still remember justifying it to myself with the reasoning that it wasn't a .250; I don't think I could have resisted that.
And as you might have guessed, before the summer was over I ended up buying, for the same price ($250 asking, $225 + tax out the door) a sporterized 03A3 Springfield with nods of approval from my elders.