I'm not sure if this answers your question, but I have set up Outlook Express to operate my Hotmail account. I don't use read receipts but I would imagine you could use the facility as normal via Hotmail.
You can't do it directly but there are a number of third party email servers who will track emails for you (the one that immediately comes to mind is didtheyreadit.com) they provide a plug-in for your browser and your outgoing mail can be routed via their servers. All of these services charge but also most of them allow a few emails for free every month so you could get maybe 10 free receipted emails a month through them.