In the old days, when everything was analog, you could capture the closed captions (CC data) if you recorded to MPEG-2 format, using an MPEG capture card or a DVD recorder. Indeed, the ATI All In Wonder Radeon series cards, and the Hauppauge PVR series cards, had this ability.
I've admittedly not watched HD capture cards closely -- mostly because they work best with ATSC or open QAM, neither of which I would use that often (as the shows I like to record come across encrypted QAM). I did some extensive testing of Hauppauge HD cards back in 2009, and I vaguely recall it was recorded the CC data via WinTV -- but I wouldn't swear it, as it's been more than a year.
Generally speaking, the retention of CC information isn't so much an intended feature as much as its simply the lack of removal on the part of the card. CC data comes in on a line that's untouched by some cards and software. Converted to AVI, you lose it all.
For the most part, I can lament your situation, but not too sure I have much help. The crossroads of 32-bit and 64-bit architecture, mixed with a couple of close OS changes, mixed with SD to HD transitions, has left us with a menagerie of broken hardware and software, many of which have Q&A solutions that are simply "ain't gonna happen" as the ultimate conclusion.
In order to help you find an answer, I'd at least need more info on the specific model of capture card, the OS, software you've tried (including versions), etc.
DScaler can sometimes work as a decent capture tool. It's not the easiest program, but based on your past posts here, you're not a typical computer/video novice -- I think you could muddle through it and understand most of what's going on.
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