I began with Live365 in 2001..almost 10 years ago.
Currently I'm running with the P4 package and am expecting an upgrade to PRO within the next several weeks. (you are not allowed to run any of your own spots or promotions on the audio stream on the "P" (personal) packages.) Because it appears we will have a couple of on-air sponsors shortly, I have begun preparing to make that upgrade.
The things I like: the package covers all the royalties; the "basic" mode provides a quick back-up in the event of power failure or Internet downtime; Live365 itself has had very little downtime over the past five years; and they now gave 'switching" from live to basic, or vice-versa, without dropping all the listeners. That used to be a pretty big issue among Live365's broadcasters.
Things I'm not so crazy about: your station has to be PRO to get a listing on iTunes; the requirement to log-in to listen (even for the free slots, so this seems a little burdensome to some folks); and the number of ads in the Live365 free listener streams. The advertiser spots I understand, but the VIP membership ones are maybe a little too frequent.)
I know LoudCity is somewhat similar in some respects, but I have not used them so can't comment on their services.
I'm developing my station, WJJD Big D Country, into a "local" internet station, meaning it will operate just like a local station - only the delivery method is different. Before, I was hesitant, because everytime I'd go from live back to basic mode the listeners would be kicked off and have to re-start their stream. Now I'm doing a Monday-Friday morning show and some Sunday local programming.
I hope this helps.
Alan