I heard an idea once from Alan Rowoth that I thought was brilliant was advice to a young singer/songwriter which could apply to a band. "Young" being the key adjective.
After college or so, pick a major metro area to live in that has a huge music scene within a one day drive. You could live in the Philly area and play New York, Boston etc. Live there for 2 or3 years until you know the town and gigs inside out and build a large email list and then move to another area like maybe Chicago, going back to play favorite Philly, Boston, N.Y. venues ocasionally. Next move again, maybe to San Francisco. Repeat.
By the time everybody is in their late 20's or early 30's the band, or duo or solo act will have enough places to play to make a living with three geographic locations as far as touring.
Lots of work but very doable if you have a dedicated band. (The idea probably works best for duos and solos obviously.)
All week I struggled with getting my podcast up on itunes - prettygoodgig.com. I set up hosting through godaddy.com, installed wordpress, and used feedburner to establish the RSS feed. It looks like feedburner would have all you need but I could not get my image to show up in itunes! No artwork at all. I also was missing the author tag and some other stuff.
While searching around I saw dozens of posts that said "can't get my image to appear in itunes using feedburner, wordpress etc."
During my search I came across powerpress which was rated very highly, so I installed it and struggled with that for days. Nothin'! Nada!
While looking at the site for the podcast called audionowcast, one I really am a fan of, for the information and humor about all things audio, I discovered they used podpress which was not as highly rated but should be at the top in my opinion because everything came together after installing that plug in. I did end up using a separate player for the mp3s of the podcast, and I also installed my itunes image in the wordpress "Resources" folder. If I had this step by step along with the other info I found about starting a podcast such as the Apple podcast help, it would have saved me 20+ hours of fiddling.
Lastly, to get an image to show up in album art on the itunes page, you embed the jpg in the mp3 file. With the file loaded into the itunes program, click on get info for that file, choose album artwork, drag the image to that location. The artwork shows up in the little box on the bottom left of the itunes view. After that upload this new mp3 to your podcast site. I had already done 4 episodes, so I had to reload the mp3 files and change the name of each one too.
Still working on trying to get the image to show up in search results!
This week was like a college course! Hope this helps!