can you mount a crank out awning?

The base is one thing but what sort of wind will the umbrella itself withstand?

An awning off the pilot house wouldn’t cover the seating area unfortunately

I feel like I just wouldn’t be outside if it’s terribly windy so I would just close the umbrella. My worry is that the base wouldn’t be strong enough to hold the entire thing down. I guess I’m just thinking of my friend’s umbrella that we borrowed that only had 30lb weights on it and I thought I was going to die when the umbrella started tipping over

You can secure a sun sail on your terrace.

There are all types of retractable awnings.

I worked in a palce with aroof top patio and no way could we keep the umbrellas from getting airborne even when the base was really heavy the wind would get the unbrella spinning in the stand and then the screw holding the umbella would break and off the umbrella would go. We finally did sails at least when they tore loose no one was injured . I would do ails and I agree there are always ways to attach them . I love roof top terraces but they do present issues for sure . You could do some of those heavy stands with posts to attach the sails to and that IMO would be the best do the sails out of solar shade material so that the wind can go though I think that would work

Look into Tucci umbrellas (Restoration Hardware carries them). They are crazy expensive, but, they are extremely well constructed and have different base plates, including bolt down versions which may suit your rooftop location.