You (probably) won’t regret it: New vs. Used Equipment
Quality equipment does cost more up front, especially brand new. However, it sounds better, can musically do things that cheap equipment cannot do, retains its value longer, and possibly acquires more character with age.
Cheap equipment does cost less up front. However, it doesn’t sound that great, it can’t musically do everything you might assume it could from only having heard or seen quality equipment in use by professionals, and it usually breaks down worse with age.
Used equipment has a discount, regardless of quality. Cheap equipment is super-cheap used, while quality stuff can cost close to or more used than it did new.
Possibility 1: You do end up doing music for a hobby or career
If you own cheap equipment and you are doing music for a hobby or career, you will just end up replacing the equipment with quality stuff at some point. The cheap equipment will not yield any money back because no one really wants to buy or use it. What cheap equipment doesn’t get sold will go into disuse or disrepair quickly, or at worst, will by its presence in your rig limit your musical ability. Case in point: cheap distortion pedals. Since they have limited dynamic range, you end up buying other things to make up for them, and then finally you replace the source of the problem. Buying a good pedal up front would have avoided the other purchases plus the limited dynamic range in the first place, allowing you access to the good tones from the beginning.
Possibility 2: You decide music isn’t for you
If you decide not to continue with a musical hobby or career, any aspiring musician will be happy to purchase your used quality equipment. In fact, it may even be worth more than what you initially paid for it if the local supply:demand ratio for your exact stuff is right. You can rest assured that your good equipment will be put to use for many years by many other talented musicians, as the good stuff continues to sound good for a very long time.
Thus, I highly recommend purchasing quality equipment used. That way, you are getting both the quality and a somewhat reduced price. If you buy quality used and sell back quality used, you will recover close to 100% of the cost. I have burned through a lot of cheap gear, and now with my current quality rig, I do not anticipate doing anything but repairs ever unless I have to replace a unit, in which case I will replace with an identical quality item used.
Image credit: http://www.flickr.com/photos/roadsideguitars/ / CC BY-SA 2.0