It sounds like you are ready for the change. If you love your stylist then I would talk things over with him and see what he says, showing him various cuts and telling him you are a low-maintenance person.
The truth is -- as you can hear from the responses -- it really depends on your hair and the specific cut you've chosen. For me and Maneera, short hair (in the right cut for us) feels like less work; for Jeanie and others, it feels like more.
I can't really comment much on the last two cuts you showed and whether they'd be less work than the first. Just because something looks a little loose and "messy" doesn't mean it would be easy to take care of. It can take a lot of work for those "messy" cuts to look messy in just the right way, LOL. At least that is my experience. But again, your mileage may vary -- it all depends on your specific wave, hair texture, and tolerance.
Also, just keep in mind that what feels "fussy" to one person feels "low maintenance" to another. Take frequent haircuts, for example. To me, that doesn't feel like a problem at all. Why? Because I get 6 weeks of wash-n-wear in between the cuts...but possibly also because I have a flexible schedule, live in a town where I can walk to the salon, etc. To Jeanie, frequent cuts feel like a hassle. Why? Well, maybe her schedule is more packed or less flexible than mine, or her stylist may be less available, and maybe she doesn't get wash-n-wear in between cuts. So compared to her longer hair, it feels like a lot to invest. And there's no denying frequent cuts entail more expense, so factor that in, also.
Courses for horses, as Angie might say.
Good luck with this! It's fun to go for a big transformation!