I don't like FREE. But, as a former player from 2006, I wouldn't have paid $5. Or maybe even a nickel. FREE gave me a reason to try it.
Nerding out a little:
I always thought it took someone 3 seasons to take the HBD hook. By then you've got a decent idea of what you're doing and the players you drafted are nearing BL-level if you had any idea what you were doing in the draft. I think it might take 2 in HD. You don't have any players that you recruited in S1. You'll probably suck. You'll get your 1st recruits but, unless you're really paying attention, your 1st recruit class won't be all that. But, by your 2nd season, you're figuring things out. You'll still be terrible, mostly crappy players assigned to you and your halfass 1st recruiting class won't help much, but you'll feel better about what you're doing. And your 2nd class will be better. If you've learned, you'll be looking forward to your third.
So maybe a free season, a $5 discount season and 3 for $20. By 5 complete, you're in.