IMO, Masters won't matter much for getting an airline job. If you want to move into management at an airline down the road, then it would matter -- you could get the airline job, then get the Masters.

Can't speak to the VR squadron option.

If you don't get into the VR squadron and try to build your fixed wing hours elsewhere, it will be a long road. Certainly do-able, but you will need to either (1) not have a spouse and family, or (2) have a very supportive spouse who is willing to accept the pay cut for quite a while. It is a tough industry, and luck plays a large part in how well you will do. You get hired and then you hope your airline hangs in there long enough for you to build your hours.

It sounds like you are dedicated to the profession, and that is the ONLY way I would advise continuing on the path. You really have to love it so much that you can stick with it even when it breaks your heart.

Best of luck in whatever you decide, and thanks for your service!