The actual difference in riding a 800cc or 1500cc cruiser is not that big it's not like sportsbikes that increase by leaps of about 10hp for every extra 100cc's. So I don't think that you couldn't get the 1500.
However from your post I'm geting the feeling that you are uneasy about getting back into riding, maybe even a little blocage caused by your droppage. In this case I would suggest that maybe you should start looking for an 800, it'll be a little lighter ( therefore easier to handle in driveways ). It'll also be cheaper and won't break the bank or your heart when you drop it.
When you get your confidence back , you can trade it in on something else that you'll be able to fully test ride.
However from your post I'm geting the feeling that you are uneasy about getting back into riding, maybe even a little blocage caused by your droppage. In this case I would suggest that maybe you should start looking for an 800, it'll be a little lighter ( therefore easier to handle in driveways ). It'll also be cheaper and won't break the bank or your heart when you drop it.
When you get your confidence back , you can trade it in on something else that you'll be able to fully test ride.