I do like being in control of my day and arrangements as things run smoothly. When H is involved he makes half arrangements, wants to check on the weather before making decisions and I suppose I don't like the vagueness off that
Some of your pour post reminds me a lot of a thread that was on here a while ago. Don't remember the exact situation but it was something to do with the fact that if one person had planned on going out somewhere, they would go out no matter what. No matter how miserable or rainy it was - all that mattered was sticking to plans as it really aggravated them to change at the last minute.
I'm afraid you will have to accept that on days that he is around, you will need to compromise. I do understand the need to make solid arrangements - it helps avoid wasting time and it important especially if you are somewhere unfamiliar, like when you're going on holiday somewhere you've never been before.
However, spending the weekend doing fairly familiar things is different. I don't think it's unreasonable to take a more casual approach to the day. Obviously, if you've made plans to meet up with one other person, you don't want to leave them there by themselves or mess them around by being late, but other than that, I think you could afford to take a more leisurely approach.
wants to check on the weather before making decisions
Checking the weather is an entirely sensible thing to do before doing an outdoor activity. If you've planned a family outing at the park, do you still want to go even if it's raining. Wouldn't you rather wait and see? Is there a reason why you can't come up with a Plan B if it looks like the weather's going to be less than ideal?
If not, I would start to wonder if your inflexibility is the result of not being to tolerate any kind of uncertainty, even sensible ones. I'm not sure I can advise you on what to do with that because some people's characteristics are pretty innate. Maybe someone more similar to you could advise better?
I would start by assign him a task that you both agree he is responsible for on days out, like packing the bag, and try not to change it. He might fail to bring everything the first few times but if he can hold down a job, I am sure he can manage to remember everything eventually. Try to resist having a go at him or being huffy if he doesn't get everything right the first few times.
He is much more of a glass half empty type of person and that drags me down if I'm honest
This seems to be a general problem that's wider than just days out. A wet blanket is enough to ruin a lot of people's day. Was he always like that? Have you simply become less tolerant to it as the years go on, as happens to many couples?