Departing US prior to decision of form I539 results in abandonment and denial of application.

It depends and not appropriate to discuss in detail on this forum. It is appropriate to speak to a knowledgeable immigration attorney for options...

You must be able to provide documentation proving the relationship and must prove that you can support your 5 years old son at 125% above the...

Federal and immigration laws do not govern where a minor can live. Check with your state and local government agencies.

Yes, if pharmacist meets criteria and qualification.

In general, yes you may have multiple jobs on H4 EAD.

In general no. Having a Canadian PR visa affixed to your passport is not disqualifying.

Check processing times on USCIS website.

Your travel plan is allowed under US immigration law. Having relevant AOS application documents with you is recommended.

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There may be a better strategy. Consult a knowledgeable immigration lawyer for options.