Apprentice mate, 500/1600 mate, 100 ton master and the kitchen sink

Thanks for any replies in advance.

I have been fishing around this forum for a few years now and have always had my questions answered just by simple searches until now. I am finally looking to get off deck and into the house. I do meet the requirements for ab1600 ton mate, which could put me in line for the mate of towing loop hole. I will get my TOAR for great lakes and western rivers, I know both need to be separate. My question is if I get the 100 ton masters also and run on that for my 360 and upgrade to the 500 would I be able to re apply for the master of towing and drop the mate of towing? Or is it a choose one or the other situation?