I feel like I am getting a lot of how this is going to fail and not a lot on how I could make it work.
It's like going to a site about being married and asking about divorce. You will get people who won't support your methods. You aren't even non-monogamous yet. You are simply getting information. Take everything you get here as just info. Find other similar sites and start building your own opinions and needs.
I honestly would like some supportive advice on how to make all of this work.
Don't have pre-conceived notions about how poly-anything works. What you are describing could be akin to closed swinging, or even polyamory, depending on the grouping you follow. Try not to build expectations around the relationships you or your partners get into.
The trick to all of it is to make sure you stay respectful of those involved and stay true to yourself. If those come into conflict, be true to yourself.
Another book to try is
Opening Up. I connected with it more since polyamory was only a part of my non-monogamy. The book itself is about every non-monogamous model, and isn't wrapped around a bunch of hippy-dippy stuff. For the record, I enjoy casual sex with partners, but did realize that I could love them. I was what would be considered a swinger for almost 7 years before I fell into poly
amory.
You do eventually stop feeling like you are cheating. It takes some time, but it does eventually happen, as long as there is trust between you and your SO.
Becoming polyamorous, moving from what was close to swinging, was a brutal experience for me. It meant months of re-evaluating. Fucking other people wasn't a problem, but loving more than one really kicked me where it hurt. My wife and I worked through it, talking a lot, and started dating. I began a really important relationship in my life, that was sexual and loving, without my wife. That jump and learning curve really helped.
I don't have the negative feelings towards swinging and controlling emotional attachment. People can do it, and people can succeed quite well. I know many in amazing long-term fulfilling relationships. If that's what you want. It takes work, and the ability to cut cords when shit happens. This site isn't really built around that line of thinking, however. (I forget what the swinging forum I used to visit was called, so really can't help.)
In the end, you seem to be heading towards non-monogamy. There are lots of variations of a theme that work. It just depends on the people involved. Don't build expectations or have restrictions you can't maintain, even within yourself.