Hi psherman,
Stunnel works configured as stated above just fine although, one thing that tripped me up; in the logs across all platforms kept seeing "already binded." Being past tense, this led me to believe that it was trying to do something it couldn't because it had already been done... And when things weren't working, I spent a lot of time trying to do stunnel without this message...
Anyways, turns out that message can be ignored entirely. I think the intent of the dev there is to just say "binded" in present tense.
Other than that, I just followed the numerous vpn tun tutorials already available on google and openwrt including one that you helped out on regarding routing all traffic to across the vpn found here;
Other noteworthy mentioning which may help others;
-stunnel issues came down to a routing vpn issue.
-couldn't get it to work with TAP
-I used CCD
-I used topology
-And used proper firewall config to route all traffic over vpn