If you've got Gold status w/ Hilton, the only way you get access to their exec lounge is if you're upgraded to an exec level floor. With the JW you're guaranteed exec lounge access.

PS - To buy 10K Hilton points would cost $100, so your valuation is a bit low on the points & Hilton points+$ would be even more.

To me it's a no-brainer - JW & use the certs. It's not often you can get a JW for a Cat 5 cert.

Cheers.