When I look at things like this I am looking at
1. Supportability: we are not always going to be the people who are supporting this and many times the next person is new, and making it simpler to read and follow is in fact a good thing
2. Functional 1: This is what it is now, but what will it, or what possibly will it need to evolve into later on? Which one is more sustainable (its a part of the functional view)
3. Functional Part 2: When doing complex filters, you start running into the probability of hitting Delegation issues sooner than later. For this reason, your first option, lends itself to a more manageable, albeit longer, but more... (imho) followable aka supportable.
4. Data accuracy. I tend to find that when people write them separately, they get their logic correct, but joined together they misplace And/Or ( and ) etc
As you start to build more columns, more filters etc, to me adding a massive And And and works, it does, until it doesn't. Will you ever hit that.. I dont know. if it faster (as supposedly ChatGPT or whatever said), well to me the jury is out on that.
When I can, I am good with a certain "level" of complex Conditional filter as your second version, but, when I start, I try to look at how can I compartmentalize it so that my subparts are 100% delegatable, and then and only then, if putting it altogether makes it work without issue, without concern for future proofing, then I go with the shorter version.
Each case, can be situation to some degree but in the end you are still looking at
1. Supportability, functional, data accuracy and future needs
For me, I would use your first 1, while bigger, but I cannot validate it against your data so thats my initial instinct only
