Do you prefer 2 high iv maxed Tyranitar or multiple level 30

I'd bring the 98% one up. You've already gone through the trouble of evolving it--it's essentially as if you caught a 98% one in a raid.

I maxed out my 98% one when there was still the old gym system and CP was critical for higher placement. Now, I would rather have the dust and candy back to evolve and power up a third

The other 3, you mean the listed tyranitars? Number 2 to 4?

I would power up the low level ones, the 98% and the 96%, this way you would have 6 really useful tyranitars instead of 4 that are 3~5% stronger than before

I have a 98/ 3604 Tyranitar, 93% 3588, and 65% 3013. The two maxed ones deal close to the same amount of damage. The weaker one obviously deals a little less. Here where it get interesting. The 98% takes incredibly less damage and lives far greater than the 93%. I don't know the exact IV spreads but the difference of two stat points shouldn't make much of a difference, but they do. Obviously they both live much much longer than the weak one.

I evolved him in the old gym system off a wild of 30 Larvitar. No regrets.that said after raids were introduced and I've stockpiled high IV Tyranitar I'm just about ready to transfer him.

I've always looked at it that you can typically only bring 6 into any relevant battle. Those 6 might as well be as strong as they can be. With that said, I've been focusing on maxing everything (breakpoints aside).

Max one or two and have at least 3 level 30 ready. Your line-up as it stands is really good already.

I have a level 38 96% then levels 30s at 91% 89% and 87%. Don't have any other 90+ Ttar even now so I'm happy with what I did.

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I like to tweak to damage break points and leave it at that. Have 1.5 million stardust, so I could max them all and still have 1 million left, but saving for Gen 3.

Since there is some legacy moveset rumor, i would say evolve all good iv one and get different combinations of ms before powering up.
Example: SC genger, db dragonite, confusion eggy, DG zam