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Buy an old Varsity, mix and match parts to make it work. You will have to make sure the front derailleur will fit the cruiser frame. You will have to add brakes as mentioned, is the frame fork set up for them? You will have to use bolt on cable stops or clamps to hold everything in place. If you had the resources to add braze-ons for this stuff I don't think you'd be asking if it will work, but that's another (cleaner) way to do it.

It's all possible. I wouldn't bother doing it myself, but yeah, you COULD do it.

If you want to make it easy,  search for a Sanctuary 7. It's already got the hard stuff done for you (seven speed freewheel out back) you'd just have to make it look like a klunker. No it wouldn't be a '50s Schwinn but it would be a cantliever fame with all the crap on it you want.

Here's a basicallly stock Sanctuary 7.

Here's mine after some changes, it's now a 5 speed IGH.

I also did a Typhoon in more of a klunker style, I thought about going with a rear derailleur but ended up with a two speed kick back instead. It may end up with an IGH also