When it comes to MMS, please start here:
Have Sprint? Have questions about Picture Mail / MMS? Read this first!
This is at the top of every forum.
As far as this issue, it does not seem to be common. The one thing the OP asked that has been discussed, is about the MMS hack which does not work anymore as discussed endlessly all over the place.
Now, to the e-mail issue... as said before, you can only send picture mail via e-mail now, the MMS hack does not work anymore, and the chances of it being fixed are slim.
nikkibee521, can you send/receive regular e-mail? Have you read the thread about sending picture mail via e-mail (there's a link to it on my announcement linked above)?
Some ISPs, like Roadrunner for example, will not allow you to send e-mail unless you are connected on their network... so sending from your device on the Sprint data network would not work.
Windows Live should allow you to send pictures attached to an e-mail unless the file is too large.
You said you are getting a cannot connect error, do you have internet accessat all?