The decision of when and what to upgrade is always a tricky one to make, so it is critical to review exactly what you need the new or upgraded gear to do, and to be pragmatic in your choosing.

1. Look at your workflows. What do you need your equipment to do for you, so that you can be creative in whatever field or genre you are working in. Remember, the gear is a tool to enable you to be creative, the gear should not be controlling your creativity. Your creativity should determine what gear you need.
2. If it ain’t broke, don’t fix it. This advice applies to upgrades as much as it does to anything else. For example, if you have a Pro Tools 7.4 system with old Accel cards, etc., and you can happily do all you need to do, then use that system and carry on using it until it starts to limit your creativity. Then, and only then, consider what to upgrade to.
3. Don’t automatically assume you need to jump to the latest technology. There is a good argument to staying one step behind the cutting edge, so that you have a reliable and proven system that won’t let you down. Clients should be looking for people that can do the job, not necessarily for studios that have the latest kit (which may or may not work). No one likes downtime when gear/software doesn’t doesn’t work properly and unreliability will kill a reputation in a flash; it will take you a long time and a lot of hard work to get back from that. So it may be better for you to upgrade to an older secondhand system because it does all you need it to do and won’t break the bank.
4. Whenever you make an upgrade decision, there will always be rumours about the next new thing which that might do this or do that and is certain to be ready next week, or next month. You should only make decisions based on equipment and software actually available and not on ‘vapourware’. Make your choices from what is in front of you now.
5. Accept that on the day you buy your equipment, it is almost automatically “out of date.” With the pace of new developments these days, there is almost always something new out which supersedes what you have bought.  But if you have bought that widget because it enables you to be creative, then it shouldn’t matter that it isn’t the latest widget.