I'm way behind the times, with a cable converter box-->original TiVo with lifetime subscription-->analog TV.

So I've got some upgrading to do. I think I know how to pick out one of them newfangled flat-screen TVs, but I've completely lost track of how the TiVo/cable box part works. Can I just buy a TiVo HD with lifetime on eBay or Craigslist and plug it in? I see people talking about "cable cards," and I see that my cable company (RCN) offers those for $2/month.

I get cable service as part of my condo fees, so I called RCN to see if I would have to pay for a different converter box and they say, yes, an HD box costs extra. That seems odd, since I'm sure most of my neighbors have flat-screen TVs by now. Aren't all flat-screens HD?

You would need either the hd cable box from RNC or a hd Tivo with rental cable card from RNC. From what I remember some cable systems use a different cable tuning system. You may need a tuning adapter. If you are an existing customer you may get a Multi user discount for service.
Depending on when you bought your original Tivo your life time may be transferable. Early on with tivo life time meant you life time. It was transferable one to a new box.

Buy you TV first to see how it works with your current set-up.

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Saint Cloud, Minnesota, where the weather is wonderful even when it isn't.

My current setup has a TiVo from 2001, which doesn't even do digital. So I don't think that can stay.

The TivoHD with cable card should work with your new HD TV, but it's not the current HD model. The Tivo Premiere replaced the TivoHD in 2010 and is also a good choice for you setup. The TivoHD shipped with a 160 GB hard drive, which is only good for 20 hours of HD programs. You can add plug in a 500 or 1 TB eSATA drive, or swap the internal hard drive for something larger.

Concerning the TivoHD and cable card from TivoHD FAQ:
Do I need one CableCard or two?

On the TivoHD, one M-CARD supports both digital cable tuners. If your cable provider only has the discontinued S-CARDs, then you will need two.

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Mr Downtown
My current setup has a TiVo from 2001, which doesn't even do digital. So I don't think that can stay.

Flat panel TV's should still have an analog (composite video) input (but possibly only 1), so as long as your TiVo still works with your cable system, it will work with a new TV.

Of course, the picture quality will be much better with an HD TiVo.