First Bike for 5'2" Rider- 2010 HONDA SHADOW

Hi all, looking for advice on picking a first bike. There are so many options and my funds are limited. I'm concerned about buying a bike that I will outgrow quickly but the idea of buying a bike with a steep learning curve is also off putting. This guy in my neighborhood is selling a 2010 Honda Shadow 750 that I haven't been able to stop thinking about. I have visions of test riding this private seller's bike and making a fool of myself and since I don't have my endorsement, I wouldn't. I would need to trailer it to my in-law's farm.

Background:

  • I'm 5'2", 140lbs with a 28" inseam.
  • I live in western WA, it's wet and rainy often.
  • I'm currently learning on a 1965 Honda CT90 (seat height 30.3", weight: 263lbs wet). It's automatic, so I am not learning how ride with a clutch. I've been using it to learn balance, turning, shifting, etc. It is incredibly stiff and I can't flat foot it, which makes it feel awkward.
  • I get some practice with a clutch in on my partner's very tall sport bike, which I tip toe around on.
  • I am scheduled for a basic rider's course

Wants:

  • My own bike, that I can hopefully flat foot and manage the weight of. To me, I think the 263lb Honda 90 wouldn't feel heavy if it wasn't so stiff and tall.
  • Something I will want to hang onto for a long time between $2000-$4000. I would go higher for the right bike.
  • Ideally (after getting an endorsement), I would like to be able to ride my bike 20 miles to work (mostly HWY) during the nicer weather. Until then, I plan on riding it around my in law's farm or rural side streets.
  • Something that has that old school cruiser or cafe racer look. I love the look of the Harley-Davidson Sportster Iron 883 but it's too expensive to learn on.

TLDR: Is the 2010 Honda Shadow 750 a good fit for me? If not...what is? Will I outgrow something like a Honda Rebel 300/500 quickly?