I've been using Max Gain Systems telescopic fiberglass masts for the past ten years. I have two of them. There weren't cheap when I bought them, and they are even more expensive now. But it so damned easy to put them up / take them down if you have access to about the first ten feet. I install mine off the back deck (with the deck being the floor of the second story). I can stand on the deck and raise and lower them with ease.
I have an MK-8-HD and an MK-6 Heavy Duty Extend. I've only got scanner antennas up now (dual band verticals, 450 yagi, 700/800 yagi, etc). You obviously cannot extend them all the way without guying them, and it should be clear that if you use it all you end up connecting to a piece of fiberglass tubing that is 3/4" to 1" at the top. My MK-8 was used to put an inverted Vee up with the apex at 50 feet. I did no guying whatsoever. It was up for years. The inverted-vee itself acted as a guy at the 50 foot level in two directions. In high winds I would just collapse it.
I use the MK-6 predominantly now, and it's secured to the side of the house at about the 8' and 16' levels with clamps. I usually have a dual-band vertical (2m/440) and a 450 or 700/800 yagi on it, but right now it just has a single 700/800 yagi on it. I did that because I wanted to extend it farther (without guying it) and so I'm keeping the antenna weight down. I usually leave the top sections off and max out at about 35'.
If you are all about doing the proper guying, I'm sure one of the Rohn's is a better choice. But for quick and dirty stuff, or if you simply like to swap out antennas every other week (I used to swap out 6m Maxons, 2m / 440 yagis, 700/800 yagis all the time) then the fiberglass masts are nice.
https://mgs4u.com/fiberglass-push-up-masts/
These are not for everyone - they are not the end-all be-all. The absolutely should be guyed (simple nylon rope is more than sufficient). If you don't need to extend them all the way, even better -- since you can leave off the smaller diameter sections or collapse them.
Because I can't / don't climb on roofs, this is my preferred option. Good luck with whatever you get.
Mike