Knowing your very active lifestyle, I would probably go for some good IEMs and a BT adapter. This gives you the option to listen no matter where you are (out, or in home). Any of the newer planars are fantastic, from what I hear. I have the Timeless, but am trying to make the decision to get the Raptgo Hook-x or the Tinhifi P1 Max. If you are wanting any kind of noise cancellation, you won't want the Hook-X though, because they are open back (but I do hear they don't leak like you would think they do). The good news is that they are both around $200, and for another $100, you can have a good set for home, and some TWS (the UTWS5 has passthrough from what I hear) for out and about. I am also interested in the up-and-coming Vulkan from DUNU, but I will probably be waiting for a while to see some more talk about them.
Just my opinion but TWS won't last as long as IEMs will, so I would get a good set of TWS (as a backup/compliment) once you have your main set secured (since you already have a good set of TWS). This is only the way I would see it, and your thoughts may be the total opposite from mine..