Indian. 7th Yr H1B, EB3 Labor/I140 Approved. H1B 7-9 yr extension in 2010. Going to Canada from USA for PR Landing(less than 30 days). Expired H1-B Visa stamp in EXPIRED Passport.

Questions:
1) Do not have enough time to go for new US Visa stamping in Canada, can I use Automatic Visa Re-validation to enter US again?

2) If I use Automatic Visa Re-validation Will it be a problem that Expired H1-B Visa Stamp is in an EXPIRED PASSPORT? I have a valid New Passport as well (No US visa stamp on new passport).

3) What documents should I carry?

4) Plan to go by air, Where will they check my Visa? In Canada before I board the flight or after I arrive in USA?

5) What happens if something goes wrong? Will I be allowed to go back to Canada and apply for a Visa at the US consulate?