The dev and user community is very active, but as with all things open-source, development ebbs and flows. The OH core is in constant development, but a binding maintainer can disappear at any time for any reason.
Automation means that when something happens, a rule is triggered and OH takes care of the rest. For example, a light switch is turned on and another light also turns on, but only if it’s a certain time of day. It’s about minimizing human intervention.
Control is the opposite: creating user interfaces so that humans can intervene at any time.
Ideally, your home-automation system balances both of these things. You want to automate anything that should happen 99% of the time, and have manual control over anything that needs to be flexible. You also want to be able to override automation in the 1% of times that you don’t want it.
The key is that your users should never have to fight your automation. For example, you could automate a TV such that every time it turns on it goes directly to a specific channel. However, that would be annoying if you only want to watch that channel 30% of the time. Automate to the point where decisions must be made by humans, and then provide simple controls for them to use.
I have a bedtime routine that shuts down my computers and turns off the lights in sequence, while also turning on my bedroom/bathroom lights. All I ever have to do is say, “hey Google, it’s bedtime”, and everything just happens without me needing to think about it.
I get that your solution needs to account for everything you’re already doing, but I think you’re probably overwhelming yourself right now. This is common when people have a lot of equipment that they want to integrate, because they don’t want to waste time on something that won’t meet their needs.
For this reason, I always recommend that people get started by setting up openHAB and then getting one very simple WiFi switch/outlet/bulb to work. Getting a quick win makes it much easier to grasp the concepts, which you can then apply to more advanced integrations. Starting with too many different things and too many complexities generally leads to frustration if/when something doesn’t work the way we think it’s supposed to, and makes it harder to troubleshoot (particularly when our pride gets in the way). It’s a longer path to your eventual solution, but getting the basics down will make it easier to visualize how all of your stuff will work in openHAB.
You can trial openHAB by installing it on pretty much any computer, so there’s no cost other than time. I don’t know how easy/hard it is to add Lutron devices, but I’d start with those to get your feet wet.