When I get into this, most of my Ohio diving will be with strangers at first, and only my vacation dives will be with family.
I just do a ton of snorkeling lately and have always wanted to try scuba.
Easy resort stuff. I can always take apart a double setup for warm clear water, where I may not need redundancy at all.
-yoke convertor for the M1
Am I in over my head yet?
Yes, I'm afraid you're in over your head, metaphorically at least. So there's no problem in thinking past your training or experience, but actually diving that way is dangerous.
The part about your post that bothered me was a brand new diver (not even certified!) saying that he'd be diving with strangers in a cold dark quarry. Even though you certainly might be correct in assessing that doubles are a better gear option than a single tank with a pony (I would almost always agree with that scenario) the point is that brand new divers should not be diving in challenging situations without a trusted buddy. Single tank, double tank, wetsuit, drysuit, it doesn't matter. If you are in a diving situation where you
need redundant air, that means you do not have immediate access to the surface and that's a big no-no for new divers IMO.
Dive safety is not about gear configuration, it's about diving with good judgement and trusted buddies that you can count on.
But, regarding your gear ideas, one thing that sticks out (literally as well as figuratively) was your plan to use a DIN reg and yoke tanks with an adapter. This is not a good idea; especially considering a DSS backplate which puts the reg very close to your head. (a good thing) Get a yoke first stage for your single tank set up and DIN for your doubles. By the time you get to the point of owning doubles, a drysuit, etc... an additional 1st stage is peanuts. Want to go even cheaper? Get either a yoke or DIN retainer for your reg and simply install it yourself as needed. It ain't rocket science.
I would suggest you take OW in a single tank, and then try both manifolded doubles and sidemount for a few dives. Do all this in warm clear water; there are excellent teachers in Bonaire, for example, that can help you with both the initial class and the technical configurations. You might really like sidemount better, in which case your whole doubles idea would change. The important thing is to try this stuff in very forgiving conditions; that will help you to build the best possible habits. As you get some experience, you can apply those habits to diving in cold dark water.
Once you have some experience, you'll find that diving with a single tank is not so different from doubles, but diving by yourself in cold dark conditions is VERY different than warm clear water with trusted buddies.