However, I think if we were in a band now, it would be easier.
The following is a list of modern technology that I wish we had when we were playing:
Solid state based portable recording
We were lucky I had my minidisc recorder. I managed to record almost everything we did, and not only did that help our writing processes, but it continues to provide a heap of enjoyment for me to this day. However, to transfer the minidisc recording to the computer (and then on to CD or MP3) it took at least as long as the recording was as I needed to plug it in, hit play, and wait. Modern portable recorders save their WAV data to an SD card (which now cost nothing). Transferring the recording to the computer takes as long as it takes to copy 1Gb over USB (seconds). I could have saves months of time.
Speaking of cheap SD cards...
Cheap portable storage
When we started the band CD burners were new. By the time we finished DVDr were starting to get cheap. Today a 4Gb USB key comes free with your coffee. The amount of money and time we spent burning CDrs of demos and live shows (which now mostly don't work) was enormous. In 2007 in the final months of my being-in-a-band, we started to use an online file server instead of burning CDrs, but copying Gbs of demo projects would still have been necessary (at least until the NBN is up and running).
Facebook
Random people were never particularly happy to sign up to a mailing list. They were always worried we'd sell their email address to someone and they'd be spammed to death (how much is an email address even worth? A billionth of a cent?).
We were always pushing people to our website, but it didn't get many visits. I think it was more for us than anyone else.
Facebook is so ingrained now I feel if we'd been able to tell people to "find us on facebook" instead of relying on email, we'd have been able to communicate better and get more people to our gigs.
I may be wrong. Maybe we had as many fans as we were ever going to get, but I think Facebook has managed to hit the nail on the head as far as fan communication goes. If only Facebook had a decent music player.
Bandcamp
Not just Bandcamp as a store, but Bandcamp as free music streaming hosting, and Bandcamp as a concept. Recording and selling our music was the most expensive thing we ever did. In hindsight we charged too much for it, and maybe that was because we paid too much for it. I'm glad we did it, but I think the expense was one of the things that pushed the band over the edge into breaking up.
I was always for putting our music online, but I could see, and can still see the point of view of the other band members. It seems silly to spend a heap of money on recording then give it away for free, even in low quality. Eventually we put a streaming player on our website... the one no-one visited.
I think if we started again now we'd have been happier selling demos on something like Bandcamp for much cheaper, potentially making more money.
I'd still like to have had a CD though. We were quite lucky in that services did exist for bands to independently print a run of real pressed CDs. Unfortunately the minimum pressing was (and still is) 500. Further, to get those CDs into a real bricksnmortar store was, and still is, very difficult. Registering for an ABN and Company Name was the most stressful thing I've ever done. These days the tax office has a form you can fill out effectively stating that you never plan to make money from your "hobby".
I'm not sure if we would print a CD again unless we did an album.
Digital cameras that take good quality video
I wish we had more video of our band. As it is we have more than I could ever have expected, thanks to a couple of enthusiastic friends at the beginning. I think though if I'd had the camera I have today we'd have a lot more video.
Internet enabled phones
It may not seem like much, but little tweets and facebook posts from gigs as they happen have a huge advertising benefit. I'm not talking money... even if just to comment to friends keeps the band in mind.
The main thing I think our band missed was feedback. I'd have loved some real feedback from non-fans, but it was very very difficult to get. I think all of the above would have helped on that side enormously.