When to order coupons?

I'd order now. The boxes like Zenith and Channel Master and Insignia are as good as they'll ever get (in terms of sensitivity & most channels received). They might release improved 2009 models, but that would be well-after the cutoff date.

If you order now, you can get two coupons without restriction.

If you wait until the FCC runs out of money (first round), then additional restrictions kick-in. You will be limited to just one coupon, and only if you don't have cable service. (If you do have cable, then you can't get any coupons.)

Stagger the coupons - get one now and another in 3 months. Then just wait till you see something good enough for your situation. It's very unlikely anything new will come out after the transition.

ordered on 9/5 and got a mail date of 9/19. Got the 2 coupons in the mail yesterday. Am going to Circuity City to get the Zenith boxes since I have free CC gift cards, and the Zenith is supported by TIVO in their software support for S2 units.

Just a recommendation, get a Zenith for your TiVo, but buy an EchoStar / DISH Network TR-40 CRA (DTVPal) with your second coupon. It has the best EPG of any of the converter boxes, TiVo-like, and it's free other than shipping. The DTVPal has had its problems, but the latest firmware, 106, fixes most of the problems. If you aren't going to use the DTVPal with a VCR, you're pretty safe.

P.S. Make sure you look at the build date near the UPC on the Zenith. I grabbed a June by accident. I am going to exchange it for a July build. Don't know if any builds from August are floating around yet.