I'm currently on OPT on my F1 visa. I need to understand my immigration possibilities depending on my future career

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In my view, I think the sooner you activate it, the better. But definitely within the petition validity period. You can apply for the visa 90 days prior to the H1B employment start date.

As long as you have a valid petition and your employer intends to employ you, you can go to your H1B status and employer at any time during the validity period of the petition, upon approval of the change of status or entry with your H1B visa stamp.

I don't understand your question about COS/CP conversion to F-1 status. You're in F-1 status now.

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You're free to go to your home country to get the H1B visa and then enter the US with the F-1 visa to continue with your education.

Your home county is the only place you can get your H1B visa stamp.

I understand that you like that idea, but you won't be able to get the H1B and F- visas at the same time.

I understand that you like that idea, but you won't be able to get the H1B and F-1 visas at the same time. The consular post wants to issue you visas only for the purpose you intend to enter the US. That doesn't mean you can't have two valid ones in your passport, but they will not do that at the same time.

At the very least, a separate trip to the consular post. But the officer might ask you what's up.

The most reasonable thing to do is to apply for a change of status from H1B to F-1 inside the US. But if you want to save the fee and take that risk, that's up to you. That's possible to do as well.

You can't start school full time and not be in H1B status unless and until you get the F-1 changes of status approved. So if you plan to change from H1B to F-1, you should give it at least six months, but maybe even more. It depends on how long cases are taking at that time.

If you can manage full-time in H1B and go to school, yes, you can do that.

Yes, that's possible with a valid I-20 endorsed for travel, a valid F-1 visa stamp, and a valid EAD.

You don't have to wait for the EAD to work. But you have to wait for the EAD to travel and return if you want to enter and partake in OPT.

The consular officer doesn't typically cancel an F-1 just because you seek an H1B visa.