You can do this all with LimeLM. The best place to start is here: http://wyday.com/limelm/help/getting-started/
Prospective customer wants a free trial product. We would like to make them register and receive an activation key via email (so we have a chance of finding out who they are) for a time limited trial.
Ok, verified trials are what you're looking for: http://wyday.com/limelm/help/trials/#verified
When they decide to purchase we would like to offer them a choice of 'renting' our downloadable software by the month ($15) or by the year ($120). In either case the renewal and therefore the billing would be automatically handled by Paypal.
That's possible using custom license fields: http://wyday.com/limelm/help/license-features/
We would also like to be able to offer the opportunity to sign up for multiple monthly or annual licenses in one transaction to cater for more than one user.
That's also possible using custom license fields. You can set the fields to whatever you want (so, for isntance, you could set the expiration date a month from now, a year from now, etc.)
Does that make sense?