entering US before L1 validity date

[James_16541]

Hi

My L-1 visa validity period starts October 1st. Apparently this visa is eligible for a grace period of up to one week before the validity period, meaning I can enter on or after September 25.

However my family (L2) and I are planning to enter the US a couple weeks earlier for vacation and for finding a home near my work. I will not start working before October 1.
So the plan is to enter under the VWP for which we are eligible, then after September 25 we will leave the country and then come back officially under the L1. When leaving the country, we do not want to fly all the way back home (since it's a long flight and we have children). We would prefer driving to Canada, or taking a short flight to a Caribbean island and come back after a few days.

I have already been advised by my attorney that this is OK, however I would like a second opinion just to avoid any risk.
Do you think this is a OK approach, or do you see any risk? Things we need to keep in mind?

Some specific questions:
(1) When entering under VWP while we have a visa in our passport, could CBP have an issue with this?
(2) How will our departure be registered if we leave via land border with Canada? I want to avoid someone someday thinking we overstayed on the VWP.

Thank you very much!

[scientist2016]

1) It is OK. Nope CBP should not have any issue. At any point of time you can have multiple valid visas stamped in your passport, and you can choose to use any one you like.
2) Whether you travel by land or air, USCIS doe not have exit records viz., there would not be a CBP check like during your entry. They reconcile this using exit and entry stamps. In your case, since you will have an entry stamp on your way in, and your I94 records will reflect this, you should not have any issues.