You are a braver soul than I!
I will probably start playing around more with Rule Machine and try to figure out some of the more complex functionality 
Thanks for this info, it's what I was looking for. I'm going to do the training to get the Essentials software before I make a decision.
Hi there came across this thread because I’m in the same position of deciding whether to go with Lutron RA2 Select or Radio RA2. I’m maxed out on Caseta switches and will either jettison them entirely for Radio RA2 or combine RA2 Select and Caseta. My house is 8,000+ sq ft, 7 bedrooms, 4 floors. Given the size I was leaning toward Radio RA2 and have one system for the whole house. However, I was corresponding with a dealer for the devices and they sent me the certification info for Essentials software. It says that Essentials only supports 100 devices. That’s really annoying, kind of defeats the purpose of the higher device limit for Radio RA2. Does anyone else have experience with this?
And yes, I know I can have a dealer install all of this stuff and program it for me (presumably with the higher device limit of Inclusive software). However, I spent a lot of money remodeling a vacation home and was sold Control4 lighting and honestly felt like I could have done a better job installing and laying out the system myself. Hence my desire to do this house on my own, my way and at my own pace. I am also integrating many other devices and intend, of course, to put Hubitat into the mix. I’m just at the stage now of evaluating/designing the right paths to go down (especially after the cul-de-sac I ended up in with Caseta).
You need the Inclusive version of the software. The way to get that is to attend a Lutron training session for RA2 Level 2, which takes a couple of days in a classroom setting, and costs a few hundred dollars.
However, with Hubitat, you can expand your Lutron system with a mix and match approach. For example, you could add a second SmartBridge Pro to get more than 50 Caséta devices, or could add a second RA2 main repeater, to get more than 100 devices using Essentials. The drawback of these approaches is only that you have multiple Lutron mobile apps. For me, I never use the Lutron mobile apps, so it doesn't matter. My own home is a mix of RA2 (just under 100 devices) and Z-Wave/Zigbee devices.
Lutron has some very old-world thinking about market segmentation that imposes these limits on systems. This all grew out of how they manage distribution channels, and has nothing really to do with technology. They impose their market segment walls through software restrictions. Not very user friendly, imo, but it's the way they do it.
When I bought my home, it had a classic RA system for part of it. Eventually, I took the online course and got the Essentials software. Then I rebuilt the system from scratch with RA2. It was not difficult. Then, because Hubitat was integrating Lutron, I took the RA2L2 training, and got the Inclusive software. It has only a few features that Essentials does not have, mainly allowing for two main repeaters. This is definitely within the scope of what a knowledgable tech-savvy person can do.
My suggestion is to really understand how you want to use Lutron mobile access first, if at all, as that is the one feature that constrains the design and layout of a large Lutron system.
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All of what Bruce said. Plus a couple other points:
Don't do Select. Essentials at the minimum. The incremental cost is the equivalent of a couple dimmers plus a few hours of training. Find a local or on line retailer that will give you competitive pricing. List is not a good guide. The programming is pretty easy.
Select does not allow you to set default levels for "on" at the physical dimmer. So they default at 100%. Some retrofit LEDs are really powerful so they need to be dimmed down IMO. Easy to do in Essentials, not possible with Select. Essentials also allows programming of fade on/off times that Select does not.
There are some higher-end controls that require Inclusive, like 0-10V, which is becoming more common in higher-end lighting. You can see the few device differences in
At 8000 sq ft you might be able to stay in the 100 device (really 95) limit if you are judicious and don't have a super elaborate lighting plan. E.g. you might not need a dimmer + motion detector (2 devices) in your closets when a "dumb" motion detector dimmer or door jamb switch will work.
Another difference I recently read in another thread here is that while RA2 Select works with Lutron's occupancy/vacancy (motion) sensors, it doesn't expose them over telnet. Thus, they are pretty much useless to Hubitat since it can't "see" them, and they are only usable within the Lutron system. This is also mentioned on the Lutron forums and a community-created Home Assistant Lutron integration Github. and "Full" Radio RA2 systems do not have this limitation.
In related news, if anyone wants a Radio Powr Savr occupancy sensor I bought under the mistaken believe I could use with RA2 Select, I have one. 
I'll be sticking with Caseta (and if they ever come out with a motion sensor for Caseta, I hope it can be exposed over telnet, though I'm not sure I'd hold my breath considering it's not true for RA2 Select).
Thanks all for the replies. Looks like I'll give Radio RA2 a try then. Am I right that at the minimum to start this, I need both the Connect Bridge and Main Repeater?
You only need the Connect Bridge if you want to use the Lutron mobile app. I have one, and don't use it at all. Others do use it. I was never big on using my phone to turn lights on/off, especially when they can do it automatically.
You do need the main repeater, and you may need an Aux repeater as well for 8000 sq ft.
There is no initial setup of devices required via the Lutron app or bridge?
There is an entire setup process using the Inclusive software, a PC app. Take the free online training for RA2 Level 1 to see what you're getting into.
I found the documentation which goes through the manual setup process of adding devices to the Lutron Main Repeater without the use of the software. I will go through the process to obtain the Essentials software either way. One question though - once the device is manually added to the Repeater, is it possible to control it with Hubitat?
There is a trick for this. Pair it to a phantom switch and make Hubitat use the device as the trigger. By phantom switch, I mean a device that is added, paired to the occ sensor, and then physically removed. The switch (which is no longer powered or even in your house) will still have it's state communicated over telnet. Expensive, but if you know somebody who also has Radio Ra 2 switches, it works. There does seem to be a delay though - if you have Hubitat use the Lutron sensor (which is actually the phantom switch) to turn on a real Lutron switch, it can take 3-4 seconds for the action to happen. Seems like the it's an issue with telnet - something is causing a delay.
Maybe I should back up and explain what I’m trying to do in this specific case with Lutron and Hubitat. I have Hue bulbs in a few rooms. I would like to program scenes to Pico Remotes to control the Hue bulbs using Hubitat, including dimmer and color settings. It was my impression that this could be done in Hubitat. Research there led me to requirement to obtain the Caseta Pro bridge. I’m almost at my limit with Caseta devices, so rather than throw more money at Caseta, I’m looking at stepping up to Radio RA2 instead.
Yes, once you have them added to the main repeater Hubitat can talk to them. However, you need to know their "integration id" number. Ordinarily you get this from the Essentials software. There is another method to find the number:
Connect to the main repeater with a telnet session from a terminal app on you PC. Credentials are username: lutron, password: integration. Then hit a button on one of your Picos or other devices. For a Pico you will see a message on telnet that looks like
~DEVICE,12,2,3
The 12 in that example is the integration id. The 2 is which button was pushed, and 3 means pushed.
Other devices may look like this:
~OUTPUT,5,1,100
In that one, the 5 is the integration id. This was a switch turned on.
Then you can setup the Lutron Integration app, giving the devices names, identifying them with the integration id, and selecting what type of device it is. This creates virtual devices in the Hubitat system that correspond to the Lutron devices, and behave accordingly.
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Perfect, thanks for that explanation, all clear now... just ordered my HE
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Sorry to return here but I've searched high and low, deleted and re-added devices and having no luck. I'm all done with RA2, have Inclusive software, integration report and can setup a 1 Pico remote system (for now), I can see the PIco in Telnet.
Set it up in Hubitat:
Created a simple automation with the remote:
But the button press does nothing to the lights. I confirmed I can control the lights within Hubitat. It seems like there is a breakdown between HE and Lutron, see below, wouldn't there be activity on one of those (last column)?
I also noticed the DNI for the Lutron Telnet and Devices seems to be changing, I'm pretty sure one of them last night was _89. Not sure if this is normal behavior or not.
It sounds as though your Lutron Integration installation is messed up. Please show a screenshot of the Lutron Integration app, and of its app status page.
Adding to this, Hubitat is definitely seeing button press on the Pico, it is logging activity on the device:
But Telnet logs no activity as you can see here:
Not sure if this is normal or not.
I have also tried removing and re-adding Lutron Integration, the device and the simple lighting rule. I also tried moving my Main Repeater, wiring directly into my router (instead of via a few switches). None of this has worked, although I noticed that when moving the Main Repeater on the network, the Pico1 device on Hubitat stopped registering activity until I removed and added it back again.
