I struggle with many of the same things. DH likes my hair long (shoulder length or longer). I think I look good with it long, but I also know that it only looks good if I really work at it.
In the past 4 years, I grew it out with gray, which I didn't like. Yes, the part that was silvery was OK, but there was the dark part which wasn't. And, I felt it made me look too tired.
So I decided to color it myself and decided to try true, natural henna (this is not the henna, you can buy in most stores which often isn't just natural henna). That is what I had in picture 2 (the one with the ice cream). I did this myself. I like the color overall, although it was a little darker than I wanted. But it was a PITA to do. Basically to get good coverage I had to get my husband to help me apply (he didn't complain but I know he didn't love doing it) and then it had to sit on my hair for about 4 hours. So this was a major production every 4 weeks.
Finally, about 6 months I decided to give in to what I really wanted to (not be frugal in this instance) and went to a hairdresser, stripped off the henna and now get it colored every weeks. To get the varied color I want, I have her do both highlights and lowlights which adds considerably to the cost, but I really like it. I'm not sorry that I decided to put this in the budget. I love the color and like looking in the mirror. Maybe I "should" like the gray, but truthfully I don't. And I like the professionally colored hair much more than I like what I could do on my own.
Length is more difficult. I am not tempted to do really long (part shoulder length hair). It is too hot in summer and more trouble than I want to spend. One problem I have is that my hair is thick so when my hair gets below chin length it will naturally dry into something that looks like a triangle (narrow on top and wide on the bottom). So, I need the hairdresser to cut it and layer it so that I don't get that look.
I love the look of it between chin length to shoulder length. In the 3rd picture, I had just gone to the hairdresser the day before and she had cut it and put in new layers to try to help me manage it better.
Here's the thing. When she does my hair, it looks great. When I run my hands over it, it is very smooth and shiny and feels great. But...then I wash my hair (with color on it, I try to wash it only a few times a week). When I do, if I take a lot of care on drying it and spend a lot of time, it looks fairly good from a distance. But, when I run my hands on it, it is not nearly as smooth and shiny feeling as when the hairdresser does it. I've talked to her and she has given me some tips so that helps some. But, bottom line, it isn't nearly as nice as when she does it. If it wasn't totally extravagant I think I would go every week and have her wash and blow dry it.
When I let it dry naturally it doesn't look great at all and I hate that when I spend 45 minutes drying it, well, it looks better but not nearly as nice as when the hairdresser does it.
The easiest, of course, is a very short style where I can just wash it and dry it in a few minutes (or air dry it). It looks OK when I do that but not as nice as when it is chin to shoulder length if I spend the time to blow dry it (but probably better than it looks at the longer length if I air dry ).
Right now I'm working on growing it out to shoulder length and seeing how I feel about it then.
(FYI - Pic 1 is in April 2011, Pic 2 is August 2011, and Pic 3 is April of 2014)