More details would be needed to make a good answer on it. For me, my GX470 had roughly 160k miles, but the white paint was defective and just falls right off. I plan to keep it a long time, and I need it to at least look half way decent, so I had it painted. I do have a really good shop in town that does a good job, gives a 5 year warranty, and is very fairly priced. For me, it was worth $1700.

Nah.  I just call it character.

I wouldn't. I'm cheap and don't care what my car looks like. My idea of improving its appearance is to put fresh metal tape over the rust holes.

It's far less likely to be stolen with bad paint and dents.

depends on who is driving it and whether another dent is probable 

I wouldn't if it's a daily driver and not a Toyota or Honda. I'd get matching panels in junkyards if it's a popular model and put those on. That's WAY cheaper than paying for a decent paint job. My 99 Ranger has 273k on it and the hood had hail damage and clear coat peeling when I bought it. I put a matching color hood on it from the junkyard for $60. That'll give ya a 100% improvement in appearance for less than the cost of new video games. 

It's expensive, it doesn't last as long as the OEM paint and who can tie up a car for a complete paint job which would take a week or more if it is done right. There was a paint shop chain called Earl Scheib that would paint any cars in one day for $99.

If I'm confident in a car, and If I don't drive much, then I wouldn't even think twice.

It's not like I'd go and get the most professional paint done with some special color changing pigments, Something that just looks good and will last me a-couple of years without breaking the bank.

Cosmetic appeal is important, at least to me.

Repainting might not be too bad of an idea considering the prices of new and used vehicles. But you're gambling that nothing major goes wrong (i.e. engine or automatic transmission failure) within the next 50,000 miles.

Since it is aesthetic only, I would not care. It usually bothers others who become allergic if they see any impurity on their car. Sometimes they make doctorate as they comment my car's exterior.

I also noticed one thing about cleanliness whenever I managed to be in their homes. Some of those live in piggery.

I made the mistake of buying a black car so I notice every little scratch plus, it has rock chips all over the front bumper and paint is chipping off. Not going to waste my time repainting the bumper since I’ve already done it before. Now if I get bad scratches or scrapes on any other part of the car that’s not the bumper, then yes I’ll repaint it because the car is only 2 years old with 77k miles

Depends on which vehicle we are talking about, but generally speaking for my vehicles I would leave it as is.

MrBob has a good point. It will never be as good as the factory paint.