I've been working with CheckPoint gear for a little over 4 years now as a customer. And my company has been a CheckPoint customer for nearly 20 years.
In a large production environment, CheckPoint is the only firewall I've ever used. Though I've seen demos from the other big guys.
I love working with CheckPoint gear. It is fun and challenging (sometimes exceedingly challenging). The product is solid and if you pay for it, support is amazing.
CheckPoint is an enormous platform and it is difficult for 1 person to be an expert in every aspect.
Here's a couple good things to say: Day-to-day gateway management is a breeze and is enjoyable to work with. Using the platform for IPSEC VPN is amazing. It's daunting and overwhelming at first. But their implementation is brilliant. Deep troubleshooting can be annoying, but it is getting better.
Here's a bad thing: Licensing - licensing stinks. It is a royal pain in the behind and my least favorite thing to deal with.
Any vendor you end up dealing with is going to have their strengths and weaknesses. The trick is finding the one who's strengths play to your objectives and their weaknesses are someone else's problem. 🙂
Here's my advice:
*Form a super-strong relationship with your sales person and your SE.
*Once you get a large presence in the platform, sign up for Diamond Support (or negotiate it in). You won't regret it.
*GET TRAINING (your sales guy is going to hate me - but negotiate this one in every time you buy something)! This is an absolute must for a beginner (and even those who have been around a long time) in this environment. Continuous education with this platform is a must for you to remain successful with it.
*Make sure you have a lab environment. Playing around in production is a disaster waiting to happen.
*Grab the Max Power troubleshooting books by Tim Hall (he posted just above me). Great resource to have on hand.
At the end of the day (or, rather, beginning) I look forward to coming into the office knowing that I'll get to play with this platform. There are some annoyances, sure. But they are far outweighed by how awesome the platform is.