Quit the negative thinking about dropping the bike! Just stop fixating on that. Nobody says you have to, and new or not to riding, it could happen to any of us at any time. One of the risks we assume when we decide we want to participate in this sport (activity, whatever you want to call it...).
You simply can NOT make a purchasing decision based on the assumption you are going to go out and lay it down somewhere! You must not do this to yourself!
Now I just sat down and logged on to post about how "enough" these bikes are for two-up riding, and saw your post here.....do NOT buy that V-star! The 650 especially will have you regretting it almost immediately, and as previously stated, even the 1100 leaves a lot to be desired. I had to get over the "bigger is better" thing before I decided the Speedmaster really could do all I need it to - two-up or not. This forum had all the answers I needed, as I, just like you, was wondering the same things before I bought. I thought I HAD to have a VTX - 1300 coming along right as I was getting ready to bite the bullet. But this forum convinced me otherwise about how the CCs don't matter so much as the torque and HP numbers, and chain drive is easy to live with, and water cooling is not a necessity....even thought I had to have radial tires at one point, just because some of the bigger cruisers had them so I perceived it to be better.
Try to get a deal on a pre-owned Triumph, if you can - they are out there, but you have to work at it. The good deals go real quick - (just ask Moe).
Hope you get what is going to be right for you. Don't count on the "trade-up" thing ever happening. If it does, it does - just don't count on it as being required.
We all wish you the right choice/decision, and happy safe riding once you are on one.
