Get your environment planned (network, what you’ll run Roon Core on like desktop/laptop/Nuc, NAS, your endpoints, OS software upgrades, rip all your CDs, etc. etc.) then…
Download, install, start your trial. If you have issues follow the guidance in the support area. Resolve your issues. Keep trialing.
*It won’t take long to identify if Roon is for you and you want to keep using it after 2 weeks.
*The Roon people are really excellent, based on previous support posts, of keeping your trial alive if you are working through a support issue so won’t so much about that.
The only time I’ve seen issue linger on the support area is 1) It wasn’t a Roon issue 2) The user didn’t do what Roon support asked them to do 
Good luck, welcome to Roon. Don’t forget to enjoy the music.