Should I apply for H1B?

Hi,

A relative of ours is currently on first time OPT till Feb 2017. He is applying for OPT extension in Dec 2016 for 24 months.

Even if the OPT extension does not get approved, he can legally stay in US till April 2017. In that case,
is there any benefit of applying for H1B in March 2017? If the H1B gets picked up, does he need to go to India for getting
H1B stamping? Is he eligible to work before October 2017?

Thank you,

He will be in 60 day grace period when his H-1 is filed. So he can stay in US but cannot work. Look-up cap-gap for this.

The H-1 can be filed w/ COS. If approved w/ COS, there is no need to get the visa stamp immediately. Stamping can be delayed until the next trip outside US.