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Visa Stamping from Canada/ Mexico

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Need some advise
I have been in the same company for 8 years(4 in India, 4 in US)
Did my graduation from India

Now I moved here on l1 and my h1 was picked up in lottery. That time my employer had not filed for green card so I had no I 140, so because my wife would lose job I decided to extend my l1

Now my h1 expires in august. I have my l till July 2020

I am planning to visit any Canada center to get my l1 converted to h1 but the nearest date I am getting for interview is May 23

1) is it a big risk to wait till May 23? Considering my h expires in august and my company will have to file extension

2) any chances of delay in processing? I have stayed at the same address for 4 years in US

3) my company is a stable product company and mostly good reputation but not a big giant name. Any problems there?

In a nutshell, is May 23 too late a date and should I attempt to get it done in India? What all documents do you think I would need in Canada
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