We applied unsuccessfully to TC50 last year. One thing that caught us out a little is that they are very strict on the no publicity before the conference rule - that's fair enough of course since they want to maximise publicity/exclusivity around the event itself. But it meant that we held back from publicising ourselves waiting for their decision (and due to the large volume of applicants, final decisions were somewhat later than advertised). Unfortunately when the decision came through it was negative - we would have loved to go, but it's not the only way to get yourself known. You've got to think carefully about the timing of your company launch and how gambling on acceptance to TC50 might affect your other marketing efforts.
Does presenting a product launch at the YC investor day count, as far as TC50 is concerned, as prior release - so to speak? Has anyone been caught out by this?
(The same question goes for the YC-competitors' demo days/investor days)
Easy answer: apply to both. Usually, you won't even have to figure out the answer to that question, the "market" will decide for you.
Just like YC, having been selected at TC50 or DEMO opens doors. Remember that VCs, corporate M&A people, etc. are swamped with requests from every possible geek who thinks they have an idea. They need to apply some kind of filter.
Depends on who your target audience is. As of last year, DEMO had the most traditional press walking the floor (NYT, Businessweek, etc). That gets you customer penetration outside of the Valley echo-chamber. If your audience is just early adopters, TC might be the way to go.