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Where do you live? How bad are the winters/summers?
It really it hard to recommend a bike for year round transport. If you are in Florida/Southeast a bike might suit you more. Snow isn't fun with bikes.. in addition to the traction issue, think about wind chill! Eek.
Doesn't seem like you are a flashy guy when it comes to cars. Why not a used corolla? Might cost as much as a new bike.
If you do go bikes, go cruiser dude. More comfort and easier for new riders.
edit: You dont *have* to life in the southeast. Any south will do.
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