I often send very long messages with no problem. I use Handcent and have it set up not to convert long messages to MMS as they aren't covered in my monthly plan but unlimited texts are.
I have also not had an issue sending to four or five people but being a bit of a billy no mates I haven't had any need to send to more! In Handcent you just tick next to who you want to send to as the stock app is clumsy in my opinion on this.
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