As someone with very long hair, I don't understand how on earth you can think that short hair requires less upkeep than long hair. If you have anything other than long hair, you have to keep going to the hairdresser to get it cut, trimmed, restyled, etc. With my long hair I do nothing other than get someone to cut it straight across the bottom when it needs a trim. By "someone" I mean anyone -- friend, family member, plumber -- *anyone* can trim long hair; the same is not true of short hair. I don't use lots of products: my hair is dead straight and difficult to curl so I rarely bother. I use shampoo, and occasionally some leave-in conditioner on the ends. That's it! I'll bet many short-haired people here use a lot more products than that on their hair. At any rate I certainly spend a lot less time, energy, thought, and money on my hair than my sisters who have short hair spend on theirs. They are always going to the hairdresser. I have not visited a hairdresser since I was 8 years old (41 years ago!). How many short-haired folk can say that?
When I once made the mistake of cutting a fringe, it drove me mad, tickling and irritating my forehead and getting in my eyes, and it kept growing and needing to be cut, and I eventually grew it out so I wouldn't have to keep cutting it and dealing with the tickling. The only way it didn't drive me nuts is if I used lots of mousse and hair spray on it and got it to stick up away from my forehead and eyes. It was far too much time and trouble.
Not that I in any way want to persuade you not to cut your hair. You should cut it if you prefer to. I just thought you might be interested to hear that in my mind part of why I love plain long natural hair is that it is so much less trouble than short hair. (But yes, most men seem to prefer long hair on women too, which I can understand might be annoying or a reason to cut it all off!)
Sarah