This is an interesting topic. Having been in your position, there are a few things I might be able to suggest that will help guide your journey.
Establish hand-signals for the observation of little bubbles, and big bubbles. Often unfamiliar divers expect CCRs to be completely bubble-free and it's confusing. Which may require explaining your mask clear, dil flush, and ascent procedure in advance.
Explain you want to be at pretty much constant depths and would prefer to "go-around" versus "go-over" so you're not constantly resetting your buoyancy and wasting gas. No need for the OC guys to follow your route, just tell them you're trying to keep gas bills to a minimum.
Consider the OC versus CCR divers positioning in the water. My group traditionally puts the CCR divers in front of the pack for two complimentary reasons. Maintaining buddy contact for the CCR divers is quite easy as you can hear each OC diver breathing behind us, and the OC divers can keep visual contact on the CCR divers. Placing the CCR divers in the back means the CCR diver theoretically could disappear more easily.
All these bailout bottles you describe are good, but if you can accomplish the dive with a single bailout, do it. One of the first things I did as a new air diluent diver was figure out six ways I could get to breathable gas. Spend your energy on fewer choices, less weight, less gear to work through cognitively in an emergency. You should have an infallible way to get to known good gas that always works. The technical rebreathers give you a half-dozen ways to breathe off them in various states of failure. You should only need more bailout for penetration/owed deco (which appears where you are headed.)
Others mentioned air share practice, but I noticed it has always worked out better to let the OC guys solve OC problems and CCR divers solve CCR problems . In theory, if you have adequate bailout to reach the surface, you have all the gas you need. By definition you are self-sufficient even if something goes boom, or the loop catastrophically tears or floods. It's not that I don't care about the OC guys, or that I'm suggesting you shouldn't plan to ultimately help each other. What I'm saying is, I've found that it's best to assign buddies within the team based on similar skill sets. The exception is a CCR diver in a state of altered consciousness.
Diving in mixed teams usually brings a lot of gas and bottles to the dive site, make sure there is an analysis procedure and the protocols are followed. It's extremely easy (for some reason I haven't yet discovered) to accidentally swap dil bottles, or grab the wrong 40. Consider an edict requiring all CCR divers to use the same diluent, and all divers to use compatible (same) gases for bailout/deco. Though admittedly at the Air-dil level this might not be a significant issue as everyone could simply run Air dil, and a bailout of air if you're really trying to simplify it.
You should be practicing a bailout on each dive with a CCR. I have found the best time to do this is at the bottom of the descent. My dive team now expects to see me bailout and I get to practice a skill without causing concern. In addition, it tests my bailout capability, charges a breath in the hose, and may help keep water out of the regs if that is a concern.
Establish a signal for "I need to make an adjustment to my rebreather and I'm in control". I've had a time or two where I wanted a Dil Flush as my Po2 was slightly hot and didn't want to do it because it might cause people to rush over and rescue me. So you'll want to work those details out in advance.
Mind your PPN2. Whether you acknowledge it or not, the technical CCR is a bit more demanding underwater during times of abnormal operation. When I transitioned, I felt narcosis was a far bigger factor on CCR than OC and immediately began using 21/35 as my "air" dil replacement gas. It's not much more expensive than air, it's easy to mix (1000psi of He, top with premix 32% to 3,000psi) and you benefit from a reduced END for up to several hours on for a couple dollars. ...And you'll be logging Trimix dives if that matter to you.
Good pre-breathes, Always bring a bailout, and never enter the water with any known fault.
Best of luck.