I would guess that most painters do worry about overspray landing anywhere it's not supposed to....at least I hope that they do. Covering brick and stone is difficult because tape does not stick well to it and even if you do get it covered there is a chance that the force of the sprayer can blow the tape right off again. One thing you can try is a paint shield instead of plastic but that often requires a second man up high with the spray guy....you can't hold a shield and spray and hold onto the ladder yourself. Really though, this sounds like something that would go a lot faster if you did it by hand rolling out of a bucket. I would look at the prep involved and probably decide pretty quick that it's just not worth it. Besides, anytime you spray wood, it has to be backbrushed/backrolled so that the paint penetrates the wood....when you just spray it and leave it most of the paint just sits on top of the wood. So ultimately all the sprayer is doing is getting the material on the surface....you still have to work it into the wood pores somehow, so how much time is the sprayer actually saving?

I found this one - link below. And a lot more by google searching "wet look brick". Here is a link that might be useful: Stone Enhancer

Still have to stain the ground a light grey, but what do you guys recommend for seating? It’s a pretty large space but don’t want to put too much money into it since we’re doing a screen in closure in the back that is taking a lot of funds. Also everything on the porch is still going.

This brings back memories as I lived in the North Dallas area in the 60s. Your trees are wonderful. I would focus on making significant changes to the landscaping to update the exterior of your home. I do think getting a more MCM front door and painting it an accent color—teal or a bright green would be interesting and draw attention to it. Get rid of the wrought iron gate and put in one with cleaner lines. Get a new porch light in a rectangular shape. If you search this site for MCM exterior I’m sure you will find examples that appeal to your taste. Definitely get rid of the shutters! If the pole light in the yard isn’t functional and you don’t need it, I would remove it. Get rid of the ground cover under the large tree on the right side of the house. All of the landscaping is so mature it would be best to start over with a fresh design plan. You can work with one of the local nurseries to design and install new plantings. I think re-landscaping like some of the pictures Beth H shared would make a huge statement — just decide if you like the more structured looks or curving beds since either one would look fine with the house.