Can one product be in two membership levels?

I’m converting from Membership Simplified by OfficeAutopilot, which allows me to have a product in two levels:
product membership
Gold membership where all products are available.

Is this possible with S2? Membership Simplified does now work with my premium theme nor with other themes I’ve tried and I’m looking for another solution, S2 seems to have everything I need so I’m very hopeful!

I’ve had a look at Custom Capabilities, which seemed to answer my question with: yes.

But – this membership will be adding new products all the time. From what I understand, each time I add a new product I’d generate a new custom capability for that product at Level 1, which is fine. Then I’d need to generate a new paypal button for the “Gold”all access custom capability. Is that correct?

Would members already in that Gold level then have access to the new products without having to purchase again?