I don't know about "pot shots", but they have mentioned several times how they come in "crystal clear" which is definitely a snide remark on 1440.
The thing about podcasts though is they are cheap. EST has what - 4-5 guys on the payroll (Dusty LTE, Iwanyk, Gazzola, maybe Youtube Trev)? Livestreaming on the internet itself costs almost nothing. The talent itself produces their own content.
Bell closed down TSN 1290 in Winnipeg 2-3 years ago, but Winnipeg Sports Talk is going quite strong (though on an even leaner budget - only 2 guys).
1440 - Gregor is basically renting the station from its owners. But given how it was previously broadcasting oldies out of Wetaskiwin it can't have been making much money. Dusty at one point mentioned off-hand it would cost "hundreds of thousands" of dollars to get his show on the radio, so that at least gives us a rough ballpark.
So the costs of broadcast radio are higher than livestreaming, but it's certainly possible that it's cheaper to do at 1440 than 1260. 1260 was owned by Bell, an enormous national company, with all of the costs that might come with that. 1440 (call letters CKJR) is owned by another national company, Stingray Radio, but all it's stations all seem to be rather, how to say it, low-budget, so it's quite possible they can run a station more cheaply than Bell.
So I dunno for sure. I guess I would be most worried about the 1440 podcasts, just because they need to cover the cost of the transmitter, but I suspect Gregor knew what he was getting into. The EST guys, they might have gone too big with running multiple shows, a physical office (don't most podcasters work out of a home office), but again I think they know what they're doing.