While I'm certainly leery of taking on too much in annual fees (or over-valuing the benefits that come with them), I think this is a unique situation. First, by upgrading to the Surpass offer you are explicitly agreeing that it's worthwhile to pay a $95 fee for 150k Hilton points. Second, while the Aspire comes with an annual fee of $450, if you have already committed to the Surpass upgrade, the increase in annual fee is only $355 at that point. And since we've already agreed that it's worthwhile to pay $95 for 150k Hilton points once, if you're willing to do it again that's just $260 of additional annual fee that needs to be justified on the Aspire. The Aspire then comes with $250 air credit (per calendar year), $250 Hilton resort credit (per cardmember year), and a free weekend night about 8 weeks after the upgrade. Assuming you can make some use of these benefits, I think that remaining $260 fee I mentioned can be worthwhile.
I think this was a slam dunk a few months ago when you could cash out the air credit for gift cards to be sold. But even still, there's a lot of ways to get good value out of it.