When is a pony a candidate for rehairing?
When it bothers you.
Are you collecting for other people or are you doing it for yourself? If all you see when you look at one of your ponies is the haircut, then rehair, because it's not supposed to bother you.
Ponies are supposed to make us happy 
If rehairing will make YOU happier, then do it.
THIS! If your collection is just for you, and you don't really have plans on reselling (of course that could change later, but you know what I mean), then go for it! If it bugs you, fix it! They're for your enjoyment, so make them look however they need to in order for you to be satisfied with them. If there's a consequence for the rehair you're only going to meet it if you sell down the road, but if it made you happy with it as part of your own collection, then it would be worth the miniscule monetary hit that you might take on it.
There's never going to be a standard, set in stone answer as to when it's appropriate to do certain resortations. Some people are always going to want ponies as original as possible, no matter how grody they may be. Chances are, if you go to resell later, those people won't be interested because they probably have that pony anyway! It's a lot easier to find a manky pony than a pristine one! It's only the super picky collectors you'd have to worry about. And even then, the super picky ones would probably rather have a good rehair than a blank spot in their display cabinet. Especially if we're talking about regular release G1s.
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