Before you buy anything, I think you should have a solid plan in mind, for what you want to be able to automate, and how you want to be able to control it, and from where.
For example, if you're contemplating the purchase of a controller, a pump and an SWG, you'd be ripe for a Pentair bundle. Pentair's IntelliFlo pumps are among the best out there. And later adding a Pentair acid injection system to their SWG is a DIY snap, and they work hand-in-hand in ways other SWG and acid injection systems can't. You can control their pool automation controllers from the equipment pad, a smart phone/pad or a computer, from home or while away. The controller has built-in support for pool/spa control, solar heating, gas heating, the SWG and pump scheduling. Way more control than you'll get from that $63 timer.
Coordinating that timer with your existing pump and an SWG is possible. It would "sort of" work with a VS pump. It's dangerous for an SWG to be powered when the pump is off, and your little timer would not be used to schedule or control the newer VS pumps. They require full-time power, and have electronics on board that do the scheduling, so you'd use the WiFi timer to schedule the SWG. If those two timers ever got out of sync, and the SWG was powered on when the pump was not pumping, that would be bad. Pentair's controllers don't allow that to happen.
Some of the Pentair bundles come with actuators that could be used to automate the pool/spa modes. So with Pentair automation you could warm up the spa on the way home and have it ready for you upon arrival. I've got an actuator on my vacuum system that is controlled by my automation controller, which allows better flow control through the vac. That WiFi timer would not be able to coordinate with the vac's booster pump, you'd need a second timer for that, wired to the first one so that he booster pump could not get powered on without he main pump on. You could conceivably coordinate existing pump, booster pump and SWG safely, if you had three of those WiFi timers, which you could wire such that the SWG and booster pump would not get power unless the main pump was on, but I'm not sure if the 2HP limit would come into play. But you wouldn't be able to control the heater, nor remotely switch pool/spa modes. Pentair automation can also control dual heating systems (solar and gas, for example) to select the best heat source automatically or manually, for pool or spa.
Robots get good reviews around here. I prefer my suction-side vac. I used to have a 280, but I didn't like it, and I didn't like having to run that second pump. I was able to convert the pressure port in my pool to a suction port, and now I connected the vac to that. You could probably do the same if you wanted to. Swapping out your one-speed and booster pumps for one VS pump would definitely pay for itself in time. Plus, your pad would be so much quieter!
Full automation will definitely be more expensive, but you should look into what if can do before you buy anything, because you want the pump, controller and SWG to all be of the same brand for maximum performance and features. And automating everything, as opposed to just the pump, might be worth the difference.
So put together a schematic of your system, and think through what you want to be able to do, and then post all that here. We'll have a look and make some recommendations. Then you can study a few owner manuals to see if that meets your needs and budget. All before you buy the first component upgrade, so that you don't end up with something that doesn't fit your plan.
Or just post your credit card number and I'll order you a bunch of new gear. I'll be happy to spend your money for you. I'm nice like that!
Edit: sorry, I just realized I shared a lot of that, jokes and all, previously in this same thread, but you get the gist...