I thought it worked okay in the 90s (besides the crossovers) in that Tim had his book and his supporting characters, and his supporting characters didn't generally show up in Batman (so I would not have ever considered them Batfam). But Tim was still young and learning. Dick wasn't as spun-off in that era as earlier, and I do think the distance he had earlier helped, and he still had more distance with Tim. Whenever he's with Batman, he doesn't shine as brightly because someone decided he absolutely had to be inferior to Batman when they are together. I don't know if it's to preserve rank or because it happens more often in Batman books and Batman's the star (the latter, though, doesn't seem to apply to Batman in other people's books). I almost dread them working together sometimes, because there is too often a "put him in his place and his place isn't equal footing" element.
I think these worked, even if I didn't love them all. I think it helped that many operated independently and did not work for Batman, did not use his cave, did not live or even have dinner at his house, etc. Now, certainly that's happening now, but in a less palatable way, since instead of them just being independent operators, they're being diminished/disregarded by Batman.In the late 90s early 2000s, they had the following members running around in costume, and back then it worked quite good:
1. Bruce
2. Dick
3. Tim
4. Barbara
5. Cass
6. Steph
7. Selina
8. Helena
9. Jean-Paul
So I think that's about the maximum you could do. Of course it is easier with less, and I'm not sure if the current writers could handle that many characters.