A person is currently on B1 in USA and has spent over 4 months. His port of entry is 6 months(late Feb). His company in India wants him to come back and apply for H1 in feb. 2 concerns

1) How advisable is it to spend around 5+ months on B1 visa
2) Is there any impact on H1 application, considering that he just came back 5+ months on B1
3) Is around Feb too late to apply for this year's H1 visa

Other option for him is to come back right now(4+ months) and apply for H1. Does that make any difference, spending 4+ or 5+ months on B1.

Please reply soon

He must leave US before last date in I-94, or he will be overstayed. If overstayed, he will not be eligible to obtain any employment visa in US.