I personally prefer the first one (although could be biased since I really like that actual haircut). I think you should go for something like that, or just dye it in way that your roots won't be an issue or you could just get sucked back into the cycle of dyeing it a lot to maintain a certain look and end up damaging your hair again. That being said, the colour in the second one is nice, so why not go for highlights in that colour, or ombre is always a cute but low maintenance look. Then you could keep your hair in good condition by just doing a deep condition on the ends and keep the top half naturally healthy. Hope I helped!