Previous iTunes purchases

I've recently looked on my hard drive and the majority of the files that are on it is movies/shows purchased via iTunes and if I'd delete selected content but opt to keep the files when prompted to do so, deleting the files wouldn't really be any good. So the question was..if I deleted selected content and opted not to keep the files and empty the recycle bin would the previously purchased and now deleted content still be available for me to re-download at a later date via iTunes' purchased category in the iTunes store? Or once I'd delete the content and the files would I have to re-purchase the content?

I've crossed this bridge before and it looks like I'll have to cross it again.
I made my earliest purchases from iTunes using a (dot)Mac ID that I had when MobileMe was called (dot)Mac.  I let my (dot)Mac subscription  lapse for a year or two due to little use.  When (dot)Mac was re-invented and renamed MobileMe, I renewed my subscription.  Unfortunately, because I let my original subscription lapse for so long, I could not re-activate my original (dot)Mac e-mail addy.  "No problem"' I thought.  I simply accepted an e-mail addy with the new Me.com suffix.
I wanted to use a single ID and e-mail addy with all of my activities, so I made new iTunes purchases using the new Me.com ID.  I asked Apple Customer Support if they could transfer my purchased music to my new Account.  They said no due to legal technicalities with the accounting records that they submit to the content providers.  Fortunately, my iTunes purchases that I made with my original (dot)Mac ID continued to work in iTunes.
Now that Apple is offering a syncing feature through iCloud, I already see that my music from disparate accounts won't collectively sync. 

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    http://support.apple.com/kb/TS4357
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