H1B-H4-Travel-Stamping-Extension

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Please help me with below clarifications.

H1B/H4 visa in passport expired on May 30 2019. New I797 extended up to Oct 30 2020. Planning to visit India on June 1^st 2020 and return on July 15^th 2020 and dependents return on July 30^th 2020. Planned for visa stamping on return up to Oct 30 2020. Extension will be filed on Aug 1^st 2020 after return to US for H1B/H4. Passports are valid above six months and working for same employer.
Questions:

1. Can I initiate H1b/H4 extension on July 16^th when dependents are in India? Are Dependents should also be in US for initiating H4 extension?
2. How many days in prior H1B extension be initiated? Can H1B/H4 extension initiated from outside USA? How many days in prior to visa extension cannot be travelled outside USA?
3. Can I initiate H1B/H4 extension and travel to India? Who can/cannot travel during H1B/H4 extension in progress? If traveled what are the chances of approval?
4. Will there be any issue at POE with 90 days visa duration? What should be the visa validity to enter USA?
5. Will there be any issue at visa stamping for couple of months up to Oct 30 2020 (planned visa appointment June 1^st to 15^th 2020)?

I know I am asking multiple questions, but I thought of adding all together will be helpful for other folks with similar situation.


Appreciate quick response.

Thank you.