It depends on the name and the niche. If there's always going to be strong demand in a high value niche, by all means play the waiting game as it's a matter of when and not if you sell. If it's a brandable, you might only ever get one offer and if the price isn't right you'll lose out on making a sale. When I say brandable I mean purely invented word combos.
As far as price it based on what you paid for it, I agree and disagree with this logic. If it's future tech that looks like a very good bet and you're already receiving interest when the market is in it's early stages, hold and be patient.
But if it's a low-mid value niche, where end users marketing budgets are generally going to be limited and domain value will remain stagnant or may even decline, let it go and move on.
Some niches are much tougher sells, because the vast majority of end users in it simply don't understand the value of a good domain. I'm quickly learning which niches to avoid and what to focus on.
I don't want to deal with end users who expect to acquire a domain for $10 and the best way of doing this is to focus on niches where strong domains are highly sought and valued.