Here's what I would do...

Keep the front end product price low. Below $50.
Have a OTO.

In your front end product, as a bonus, give them free
30 days access to your membership.

That's it. This should work well. The more value you
give in the front end product, the more it will work.

If not, change the pricing of your front end product
to a $1 trial to your membership, then offer a OTO
when they sign up.

The 2nd option is much easier to get customers with
much better conversion.