As things are currently done, it seems like you have just incrementally more information than radio does, probably smaller body of listeners, and it's run very similar to radio. It's radio with downsides and fairly limited upside. A lot of the content doesn't have an age, there are 2 year old comedy podcasts that are still funny, splice in new ads and it's like syndicated TV instead of radio; plus that potentially lets them monetize their body of work and not just the newest stuff which might lead to better sustainability, their affiliate code doesn't work 16months later and then the marketer doesn't know how they got the lead and the podcasts doesn't get paid.. The pod catchers and players can provide a ton of analytical data too, no reason to not know if your ad was skipped or not. Just seems like a bit more technology is needed and it could really boom. Likewise, if you have this targeted ad stitching stuff working, you could easily have ad-free subscriptions and pay the content creator directly.
I cut our cord and basically stopped listening to radio because of the ads, tons of ads and ads that have little or no value to me. Lately, it kind of pains me to say it, but some of the targeted ads on Facebook and some other places are shockingly well targeted. Like they're hitting me up with things I'm actually interested in. I dislike being marketed to all the time but I hate these ads a lot less and I've actually bought some stuff because of it. It's pretty advanced, whereas podcasts still seem to be mostly doing it the old radio way with different distribution.