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I have noticed a trend in people I have played and games I have watched (in person and batreps). This trend is that almost without exception the player will sacrifice the ObjSec transport to protect the unit inside when they could have chosen the reverse (and often gained tactical advantages). I will gives some examples below and discuss why I believe this is happening but I mostly wish this thread to be a discussion of how to make better choices about what to keep alive. Common situations where prioritizing the safety of one of these two assets will gain you an advantage. In general please try to inform and discuss. I am also not perfect so if you see flaws in my reasoning please enlighten me and teach me a better way.

The most common situations I have seen this are;
*Dire avengers in waveserpents about to be charged (usually by MC X as serpents are not quite as effective at removing Sv3+/2+, T6+ MC as they are most infantry). Serpent spam is popular so I have seen this exact situation at least a dozen times where a MC gets within charging distance of a serpent and the CWE player has the choice of trying to move back, shoot the serpent 1 turn, then let the serpent be charged (and destroyed), after which the dire avengers inside get to shoot once, overwatch, and usually get run down the next turn. This usually happens mid to late game and is normally a combined effort with the midfield not being a safe place to escape to due to other units. IMO and what I usually do is unload the dire avengers, shoot the serpent and avengers. You can then try to create distance as you were going to try already, you can separate the serpent and dire avengers to make charging one put you out of range for the other, or you can move the dire avengers up to just over 1" of the MC to block the MC's movement. You gain at the minimum an extra turn of shooting the serpent and you possibly avoid some dire avenger deaths and pinning due to an exploded serpent. Admittedly this is not a no thought reaction though as if there is significant shooting you will likely loose the dire avenger unit and get charged but it is something that should be considered.

*SM in transport faced by CC MC with S6 Sv3+. I have seen a lot of situations where a unit of SM (usually without any special weapons left during the late to mid game) stay in a transport let the MC charge and kill it and then when they come out later (without any damage done to the MC since the transport got killed) they proceed to krak grenade the MC to death as SM tend to do. I have a hard time understanding why it seems to be a forgone conclusion that the metal box needs to die before they "avenge" it?

These situations do tend to center around late game charges as melee is usually more effective against vehicles than against infantry. I believe however you can understand the point from these situations. I also believe that the situation has a lot to do with whether the transport allows the passengers to overwatch or not and whether the transport will be able to move on objectives later (ie is it blocked or immobile?). There are numerous situation where one approach would be more advantageous than the other which is where the discussion comes into play.

The reason I believe people often do not consider prioritizing transports over the infantry is that in 6ed the choice was almost always obvious as transports could not score or contest and thus the infantry could win you the game while the transport could not.

BTW the dire avengers in waveserpents I have found to be the most forgotten about infantry in the game. They are almost never put to use unless the serpent is destroyed where if they were exited early the CWE player often could gunned down several MC or a significant part of a "horde" type army before they ever get cornered.

Thanks for reading the long text wall. Sorry for making you suffer.

I think a big part of it is that the occupants of the transport, at least when it comes to the armies I have experience with (CSM, DE, and my friends' Necrons, IG, SM, DA) are generally killier than the transport itself (obviously Wave Serpents excluded from this list).

So if I have the choice of losing a bunch of dark eldar Kabalites or a Raider transport? Likely I'm going to let the Kabbies live, because they can actually kill things.
CSM rhino vs CSM? Rhino has a single combi-bolter and only 3 AV 11/10 hull points, vs potentially 10 3+ wounds in the unit all with bolters and more.

No point letting the Rhino live if you are afterwards unable to kill anything with it, though as you say ObjSec is starting to make me reconsider...