Test ride them all. IMO most Dynas or Softails would be a better starter bike than the sportsters. Better yet, find a cheap used metric standard or cruiser and ride it for a while.
Depending on your size 650cc-750cc is about right. I see them for less than $1000 on a regular basis. Ride it (and drop it) for 6 months then sell it.
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 2008 Ultra Classic (FLHTCU) - Black Pearl
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