Yes mimico_polak.
I agree a bit of commonsense and judgment seems to be called for. I suspect there are more reasonable people than jerks out there. What I described was rhetorical and would be a worst case situation.
I am thinking that it is best to leave a test ride till the very last, after I have had a chance to get to know the person and verify maintenance and title issues.
I have to say buying and selling in the cruiser market is different than the sportbike market. Since the demand for hot cruisers is pretty low (people don't really steal and part out cruisers or track them) you will most likely have an easier time getting a test ride without handing over the full amount in cash.
Your best time to start looking around is right now. Some people would rather sell than store. Some people are also looking to purchase new in the spring so they have (want to) dump their current ride.
Familiarize yourself with the type you want. Watch Auto-Trader, Criaglist and Kijiji for price fluctuation.
Be clear on what you want and what you are willing to spend. Be patient and. It is a buyers market come fall. Sellers market come spring. Market is pretty stale for used bike in the winter due to reasons listed above.