Even with 1,000 pounds holding down the stand - lol - the umbrella is the issue and probably will always bend/snap. I would bite the bullet and build a pergola. You could go with a portable awning when not too windy or increase the number of beams to get the maximum amount of shade. There are sails, but not sure how sturdy they are..perhaps you will hear from a professional or someone that has them.

Yeah, roof or wait 20 years for trees...

Umbrellas will always be a problem. From the looks of the houses (both in style and assumed price point), I would build some sort of pergola structure for shade.

Have you considered a louvered roof. You can open and close it and change the direction when the wind is blowing.

http://www.equinoxroof.com/product-info/

Did you find a solution? I think a sail shade would work IF it had venting to permit rain and wind to pass. i want to be able to put the sail up and not worry about sudden winds. But I haven’t found such a thing on the market. Anyone else? Other ideas? A pergola would be unsightly on the rooftop patio in this case

We have a pergola and put sun shade fabric on top for even more shade. We stapled it on with a staple gun and reinforced the edge that gets the most wind with a 2x1 all the way across. It works well, decreased the temp significantly, and you really can see it from underneath.

**can’t see it

We live close to the lake, it is south of us with an open field between , winds are horrid at certain times otherwise beautiful. We have tried almost everything there is beings we have lived here for over 30 years. We having screwed down gazebos which stayed screwed in but twisted above and ripped off but we finally found a gazebo that unfortunately I don't thing they are making anymore and was sold at Canadian tire i think its called an Essex with a cut out on the roof then a small square roof on top of the cut out. In bad high winds my husband does tie it down a bit to our railings but for the most it is the first to stand up to our winds. It has been awesome in the wind and the heavy snow We are thinking of putting a pergola beside it as we would like to extend the sitting area. I have many tropicals also that cant be in the burning sun so the extra room would help .

We had the same situation. We looked for years and settled on a Markilux retractable awning. We picked the style in a kind of pergola frame. Stands up to rain and snow. I’m not trying to promote the brand, just sharing that it’s the most wind-sturdy we could find. They said it’s tested in a wind tunnel up to 80+ mph, though we don’t sit outside when it’s that windy. Quite pricey and we had to save up. But after failed umbrellas and sails, we now actually enjoy the deck regardless of the weather. If you don’t care about rain, then a pergola could work. Do your homework about the width/height of the slats (esp) and the angles against sun at various times of day and seasons. We have one neighbor with one that’s not useful, and another who put in cross slats, which seems to work.