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I have already been doing this (Getting Better for each milestone). :)
But I only level up a PC if they satisfy the old school requirements of killing and looting during the milestone. My 2 PCs have reached 2 out of 8 milestones, but one of my PCs only has been levelled up once because they fled a fight. 

However, they are already fairly strong now--they have been lucky and found 3 scrolls in the early going. It's possible PCs may get too strong too quickly in longer campaigns...

Yeah, I think I need to add a caveat about getting better only if you think it has been a significant achievement. I usually make my milestones pretty dangerous (e.g. a significant journey or crawl) - each one potentially spanning a few sessions.