Nice work, sounds like it may have been a clear experience of 4th jhana (Equanimity in vipassana jhana terms) but either way it's almost certainly a jhanic state. There's a few things in your post worth mentioning...
I simply rested into it as opposed to working at it. I think it's something I've been developing because I had an event a couple of months ago where I could rest in awareness (I was mentally noting during the day) and it felt like stepping into a beautiful melting sauna after being frozen.
Early stages of Equanimity. Good description of it.

It was nice but ultimately dissociative and all the things I normally crave and love became less like craving more like I was satisfied but there was still a lingering dissatisfaction with that.
That's good, keep on looking as you're in the perfect place to do the damage and land Path. Keep on observing that dissatisfaction and what it is to be fundamentally dissatisfied with this state, which to your average non-meditator would probably seem miraculous. Even an experience as cool as this one isn't it. Keep going.
I went back to what I liked without meditation and with lots of self loathing (like I haven't done in a couple of years) an an addictive fervor almost like a gambler. After some more meditation with this resting awareness/void I feel more free.
Late Dark Night/tail-end of Re-Observation as it fades out, most likely your baseline at that point in time, moving up into Equanimity. Now, rather than resting in or with that awareness/void look at what it is that's still observing that since it's still transient, luminous phenomena being observed by...what?
The old habits are still mentally there but it's less "sticky" (as some here like to call it) and I only want to do them at 5% of the force than usual. The 3 characteristics are more like friends now that I can tap into anytime.
Would "natural" or "normal" be a reasonable way to describe it?
Meditation is just there to solidify what was always there.
Do. Not. Solidify.
Anything...if you're doing insight practice. Be careful, it's all to easy to get complacent and wind up back in Re-Observation until you figure it out.
Investigate it, examine it further, probe it and look at what sensations make
that up.
The desire to stay with awareness is quite strong now and that is totally new to me.
Look at that desire and what it is that you're desirous of, much as this may be new to you you're also in a good position to get into this really deeply due to it being so fresh and amazing. It's fine to enjoy it and groove with the spacious, laid-backness but if you want to get Path then keep on investigating.
No concentration jhanas could do this.
Oh they most certainly can, and much, much, much more so don't get lazy and settle for second best. If you're still seeing the 3C's presenting themselves clearly then use it to your advantage, things are super-clear in Equanimity and the way objects just appear without effort provides a great opportunity to see what's at the heart of the thing.
Whatever it is I'll just enjoy it while it's here and keep looking at the 3 Cs. I just want to deal with habits now and get on with life.
The pessimistic response to this is that you're likely to wind up disappointed if you just enjoy it without further investigation, this is because you'll go back to square one and cycle up through the ñanas again until you get it. It's still not permanent, it's still empty and it's still fundamentally unsatisfying so that means it can't possible be "it".
Look at what's still looking, what's still observing these objects arising and passing away, what's still seeing the 3C's playing out? If you're able to observe what you're calling "awareness" then it can't possibly be this awareness as that's not something you can ever observe, it's the observation and everything else so what's left to observe that? Don't fall into the trap of solidifying this into 4th jhana, you'll miss out on a great opportunity and have to work your way back to it again.
Keep on sitting, maintain your practice and don't let up.