Advice sought about upgrading my 1st Rolex

[Haili Selassie]

My first Rolex was the Sub C no date 114060 purchased at an AD in December of last year.This was my daily wearer and I absolutely loved it until about a month ago when I picked up the new Sunburst TT Sub.That watch sang so loud to me so much that after trying it on at the AD I made arrangements to meet one of our most trusted sellers the very next day.
Having always been a bit of a gold bug I really prefer to prefer the TT much more than the SS,also having the only two watches in my rotation both being subs feels somewhat redundant so I am considering upgrading to the GMT-Master 2 TT.Since I don't have 9K more after just dropping over 10K on the Sunburst a move would be contingent on flipping the 114060.So my question to the community is twofold,It seems the trade in value is about $500+ less than the similar watches are being sold for here.Would it be possible for a fairly new member with the only reference being a smooth buy to sell on the forum for a normal market price?Also what do you think about the considered move?Any input would appreciated.