Getting the itch to maybe make a trade would you do it

[hbombkid]

So I have not posted in a while but wanted to get some opinions. I stay at a 2 watch limit and to be honest that might be to many especially my situation. It has almost been a year working remotely. I love watches still but I really only wear one a couple times a month. Maybe that is the reason I am even looking at the trade. I said I would never sell my sub but to be honest I do not miss wearing it. I might have worn it 3-4 times the past 2 months. I wear the omega more but I would trade that away in a second if the right watch came up. Anyway I might be able to get this trade straight up. (Edit) there is not a trade on the table more just saw two watches reasonably priced and then selling mine. I have already found two trusted sellers that have what I want. The biggest question would be true value of the sub and omega. I have an idea what they are worth but not sure if I would get that.

Trade the following
Sub date warranty from April 2016
Omega aqua terra 2500 big size white dial blue stick

Receive the following
DJ41 blue dial smooth bezel, can do either the oyster or jubilee warranty 2018
Panerai Base warranty 2019

Why I am considering this:
Always am a fan of blue dial watches and want to keep a Rolex in the collection. I also really like Panerai. I choose the case because of the clean look. I love the 3,6,9 dial and the crown guard.

Questions
1. Would you do this trade especially straight up? I decided I would not put any money in.
2 on the DJ 41 would you go oyster or jubilee? Is the jubilee to dressy for jeans or shorts (that is really mostly my attire daily). I might dress up 2-3 times a year.