I am a developer who uses the SilverStripe CMS. I have over four years experience in everything from small websites to large multi-user internal system tools. I was originally drawn to SilverStripe in my web developer infancy because of its strong and intuitive templating system, and I've never looked back. I give back to the community by providing support on the IRC channel, through which I've met new people and learnt a whole heap of things I never would have without the tools I'm about to talk about below.
So. You're a developer who has (perhaps recently) discovered SilverStripe. That is great! You're loving how easy its sleek UI and extremely supportive framework makes your life when it comes to developing websites or web applications. However you've just come across an issue that you're having trouble solving. Maybe it's a question about how something works, what the best way to achieve something might be, or maybe how to troubleshoot a problem you're having with the system. Perhaps you just want to say "Hi" to the community. Whatever your reasons, SilverStripe has a variety of methods to enable you to contact people who are willing to offer you support.
Support can be found in abundance through the (soon to be upgraded for extra awesome) silverstripe.org (not .com, that's the company, not the community) website. First things first, one should make sure to have at least read through the tutorials. Of these, the first two are most important, they will provide a basic background to the entire system. Beyond that, tutorial 3 can help solve many questions about forms, and tutorial 5 can be useful if you're new to creating relations. Even as an experienced developer I still find myself using tutorials 2 and 3 as quick references for things I cannot be bothered to look up properly.
Beyond the tutorials (that everyone should read), it depends on your level of expertise as to where you should look for help. Two of the most common reference sites are the docs and the API. The doc site holds many references and little tidbits of juicy info to give you start-out help with whatever you have in mind to work your problem through. This includes debugging help for issues that don't involve building something with PHP (or the unfortunate aftermath of having built something with PHP in the SilverStripe Framework). For the more advanced PHP user, there is a full API documentation available at api.silverstripe.org. This is my most common port of call and holds many quick reference notes for figuring out which method to use where, what is available in your current scope, or even just checking up on the correct syntax or method signatures to be used when coding your next function or subclass.
These resources are all well and good, but what if you're not a hardcore coder and need a little assistance in deciphering what they're trying to tell you? SilverStripe.org also has facilities in place for a more personal level of support (by personal I refer to getting answers from real people - not one on one full system tutorage/getting your work done for you for free, an unfortunate however surprisingly common mistake some people seem to make).
To this end there are the forums and the IRC channel available for personal contact with other developers using their favourite system around the world. The forums are a useful place for many beginners and contains a backlog of resources regarding installation issues, module setup and problems, and fixes to those problems. The issue here currently is that many of the more experienced developers find the forums a little too simplistic for the more power user style questions they wish to ask, or perhaps you're under too much pressure to wait for an answer on the forums.
For real time interaction, enter the IRC channel! Here you will find an active community of developers, usually from countries on your side of the planet (time zones are an interesting thing like that), all at various levels of experience with SilverStripe and more importantly, the Framework. These power users are there to bounce ideas off of and query for instant help. And as an extra bonus, most of the correspondence (both on and, err... extremely, off topic) gets logged for future reference at logs.silverstripe.org.
With the handy backlog of questions at logs.silverstripe.org you can perform a search by using the Google query "<your question> site:logs.simon.geek.nz" (the logs are provided by prominent community member Simon Welsh on his server). So asking questions also helps other people in the future who may have the same problem as you. If you don't get a reply to your question immediately, please don't feel left out. Many of the people in the channel simply idle there and answer questions when they can at a later time. This is why if you're on the IRC channel it is very important to actually ask a question! Many times people arrive and ask "Can I ask a question?" - to which there is no response before they quit. If they were to actually ask their question they could search through the logs at a later point to see if someone answered them after they left. Everyone in the channel is there to help others, so ask away!
Read the tutorials. http://doc.silverstripe.org/framework/en/tutorials/
Search for examples and references on docs.silverstripe.org
Power users can make great use of api.silverstripe.org
Introductory personal help can be found at silverstripe.org/forums
Community provided live support at irc.silverstripe.org (or your favourite IRC client - #silverstripe on Freenode)
Search the IRC logs - logs.silverstripe.org
The trac bugtracker at open.silverstripe.org sometimes lists untested/uncommitted patches to known problems in the ticket's comments.
This is just a quick cap of the major resources provided for one to find help about the SilverStripe CMS and Framework, far from exhaustive. Also worth noting is the core developer mailing list found on Google Groups: groups.google.com/group/silverstripe-dev - If you wish to join in and contribute to or voice concerns about the direction SilverStripe is taking as it progresses as a system worthy of web dominance (or just lurk for bleeding edge news scoops). At every turn there are friendly people willing to help you solve whatever issue you're having with your SilverStripe system; all you have to do is find out on which of the many available mediums you wish to put your question, and then ask!
With these more interactive ports of call for help, (as with any online community interaction) a little bit of etiquette goes a long way. One must remember that this help is offered by the community in their free time, so basic courtesy goes a long way.
Please do not start off asking a question by ranting about how bad the system design is just because it's so different to whatever system you've used before. All you're likely to receive is a disgruntled "don't use it then".
We're all here because of our favourite system, and trying to aggressively convince a whole community that they're wrong is a sure way to get ignored. If you do have a criticisim, pose the question in a more approachable tone and you're far more likely to get listened to and have your opinion considered seriously.