I'm no expert but I have a couple of Contenders, and first, I'll say this,
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The barrels are marked 30-30 and .357 Win but the case says .356 and .307,
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Abso-frackin-lutely get a gunsmith to check the chambers (make chamber casts) and see what they are.
First, there is no .357 Win, but there was a .375 Win and a .356 Win so is that a typo or is that what it says? It might be possible to bore out a .357 Contender pistol barrel chamber to take the .356 Win, (ask a gunsmith) and the "Win" after the .357 on the barrel might have been added by the original owner, no way to know, I guess.
Next, the .356 and .307, these are rimmed versions of the .358 Win and .308 Win, made for use in Marlin rifles (hence the rim), and I'm not certain they are lower pressure (for the lever gun) than the rimless rounds but I think so. Will have to do some research to be sure.
Neither the .308 or .358 were ever factory barrels for the Contender, it simply wasn't up to their pressure, and T/C put them in the bigger frame single shot, the Encore.
It is possible the lower pressure of the .307 and .356 might be ok for the Contender, and fur sure, tailored handloads would be.
It wasn't case size that made the difference it was the pressure. The Contender handles .45-70 for size, so a .308 size case body will fit, but it has to stay within the pressure boundaries of the action. The regular .308 Win is simply too hot.
since one barrel says .30-30 on it, and something bigger (.356/.307) fits in it, its clear it is no longer the .30-30 that it began as. SO get a gunsmith to check it, to be certain. If desired (and I would recommend it) a gunsmith can re-stamp the barrels with the correct names of the calibers they are now, once that is known for sure.
There are at least three, and maybe more "generations" of Contender, the most visible difference is the changes in the "selector switch" on the hammer, that changes the position of the firing pin strike from centerfire to rimfire and back. There are other changes and not all barrels will fit all models.
The last version of the Contender was named the G2 but from your description of its age, it is unlikely to be a G2. The G2 works a bit differently from the earlier Contenders, we can cover that later, if anyone is interested..
I ignored the Contender for decades, (after all, it was only a single shot, right?) until, one day at a shop I tried the trigger on one. The triggers are great, and the guns are generally much more accurate than most repeating pistols. yeah, I got the bug, and wound up with a Contender and barrels for all my other handgun cartridges and some of my rifle ones.
The Contender is all about precisely placing one bullet exactly where you want it to go. If you're at all accurate with a revolver or semi auto, the Contender will show you another level of accuracy, its an eye-opening experience.
The two barrels you have, (in .356 and .307) are deer hunting guns. You didn't mention the sights. Contenders have decent adjustable sights, and are easily scoped.
I've got barrels in .22LR, .22 Hornet, .222 Rem, .30-30Win, 9mm Luger, .357Mag, .44 mag, .45 Colt/.410, .45 Win Mag and .45-70, and have had great results and lots of fun with them over the years.
Hope this helps