Syncing Sent Email

Hi,
Firstly, not the sharpest chisel in the toolshed when it comes to mail setups. And not entirely sure this was the best place to post this, as one Mac is Lion, and one is leopard, and other devices iOS.
Forgive me if I'm being thick, but..
If I answer an email on one mac or device, then when on my other mac or deivice & wanting to check what reply I sent to that email, it gives me an error message "Error Mail was unable to find your response to the message "(Blah, blah, blah)". You may have deleted the message.
I've done a fair bit of searching on this, and I'm sure it's probably just me not parsing the question in a way google likes it, or using the right terminology, but I keep finding answers to other issues but no mention of this issue.
I have an iphone 4, ipad 2, macbook pro retina, and an imac that I variously use for email in my business, (plus another 13 macs I don't email on!). It gets annoying when you have to search for which particular device you replied on to be able to read your reply.. I'm sure that this is not the implementation Apple has given us, and I'm missing something.
In case it matters, the email accounts are 2 x webmail accounts attched to my website, 2 x accounts my ISP provided ([email protected]) and 2 x Gmail accounts. All iMap.
Secondly, deleting emails doesn't alway delete them on the other devices. Also pretty annoying.
Looking forward to some help that will get me over this hump..
Pete

First check if hotmail does imap. I don't know but a simple google search should turn up a yes or no. Then I'm not sure if you can just change the present account from pop to imap or if you have to create a new account. Imap settings or different from pop in certain areas like the ports used and security settings.
Doing a google search for hotmail it seems it has gone from hotmail to live to outlook.com. Not sure outlook.com does imap but there is a section in the mail contacts and calendars section of system preferences for ms exchange which is what outlook.com uses, if I recall correctly.

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