Juppie,
You've asked some big, important questions some of which require clairvoyance to answer. However, there is a school of thought saying the market is getting pretty good for pilots in North America.
Everyone who starts in the civilian route to a flying career faces the same uncertainties you mention but most survive it to one degree of other. No reason you can't do the same. You can remove many of those uncertainties by learning to fly in the military if that is available to you.
I can only suggest you also ask your questions/seek advice in a more US-centric website like
https://jetcareers.com/forums/
Best of luck to you.