Re: Marshall vs Orange Heads and Cabs.
its about the tone. do you want to sound like a marshall or do you want to sound like an Orange.
That's the first consideration. Newer Oranges sound closer to Marshalls than the old ones with an FAC control, but they've still got a different feel and texture. I'd love to have an Orange Overdrive 80 with the FAC control while the new ones really don't do it for me. OTOH if the OP really digs the Rockerverb, a Marshall won't really do that.
Judging by his age (i.e. just getting his first job) I think he will like the orange better because it saturates better on its own. I LOVE my 800 and would take it over a rockerverb any day, but 10 years ago I probably would have prefered the orange for that reason exactly.
Also, go get yourself a part time job ASAP like your alluding to. There's no such thing an an appealing workplace when your still in HS but that extra cash will come in handy for gear purchases and maintenance.
+1
An amp with more saturation will be much more satisfying to someone that isn't used to playing through tube amps. I didn't really care for 2203/2204s when I started playing and wasn't blown away by my 2555 Jubilee at first because I just didn't have the chops to make them sound decent. When I first got my Jubilee I was using a JB and had the gain on the amp dimed and it was almost too clean. These days as I've learned to control my playing better I run the gain on about 6 and find anything more too saturated.
Another thing to consider is versatility. The Plexi RI, JCM800, and my Jubilee are all one trick ponies. It's a great trick if it's what you're after, but you're not going to get a bunch of good but different sounds from the same amp. The Jubilee is sort of two channels, but they share a gain control so the 'clean' channel is usable though not great if you've got a good OD tone dialed in. If you dial it in for the clean sound, the OD mode will probably be weak and the EQ balance may be a bit off. Both the Plexi and 2203/2204 are single channel amps. The Plexi is FAR too loud to overdrive on its own, so you'd be stuck running it clean with a pedal which I understand you're doing with the AC-30 now. Getting 70s & early 80s metal tones from a 2203/2204 requires a boost pedal which you could turn off and roll back your volume to get clean, but it'd be similar to the semi-clean the Jubilee is capable of.
With the Rockerverb or a DSL you've got two channels with completely separate gain & volume, so a good clean sound would be a single button push away. The JVM Jolly recommended has either 2 or 4 channels depending on which model you pick.