Antenna support/mast
This will do you - Antenna Supports & Hardware - Antenna Lifting Kite, Telescopic Masts, Compact light. you don’t really need a 20’ high aerial support if you’re on a hill thats already quite high!!! .
I spent some time practicing erecting one with the recommended 3 guys. I gave up and found it much, much easier to get hold of a shortish length of black waste pipe, (its thicker than ordinary plumbing pipe) and about 16" long with one end cut off at an angle to make a point. It needs to be wide enough to get the end of your mast in it. Insert the pipe into soft ground then put the mast into it. If needed ~I insert it into cracks in rocks which are easily found on most of our summits or simply pile heavyish rocks around it. It also protects your mast from getting knocked about with direct contact with the stones/rocks… It takes up no extra space in your bag as the collapsed base of your mast sits in it for transport. I’ve never had to use guy lines - the antenna wire obviously helps to keep it up.
Oh, and you’ll need a witty reply for the inevitable; "Are you going fishing? question from the odd passerby.
Aerial/antenna
I use Sota beams linked dipole - you don’t need a tuner.
You need something to sit on. Well, I do - as `i only use morse and like to sit down to operate. . Simplest is go to your nearest garden centre and buy one of their kneeling mats. If you’ve got camping kit then a couple of pieces of Karrimat or similar will do. You won’t want a wet bottom anyway if you sit down.
Shelter
Bearing in mind it gets much colder up hills than at sea level, some kind of shelter is important unless you only intend going up when the weather is perfectly warm.
As many others have said, first line of defence are walls, rocks and so on. Its surprising how a dip in the ground of just a few feet slows the wind down. I’ve tried tarps, but they can be a bit unwieldy on windy summit days and I’ve found they don’t work too well on un-even ground…
I do use a golfing umbrella, sometimes, which `i peg down. I probably get some odd looks but at 74 and years spent in the hills I don’t care.
But if the weather looks inclement and likely to rain, or you think you are going to freeze your wobbly bits solid, the ‘go to’, item is a two man bivvi bag/shelter. I’ve used these on summits in quite bad winter conditions and been quite warm.
Some have attached ground sheets which make them really comfy - but awkward to get in and out of if you have to adjust your antenna. Mine had no fixed ground sheet so i modified mine by adding half a decent sized tent material to one half of the base - so
i could sit on it and stop any wind getting in around the back.
PS. `if you use a paper logbook, do make sure the pen/pencil you use is waterproof and doesn’t run if your log gets wet…
Good luck