I think it also depends on how you plan to use the bike. While a number of guys here have done really successful long trips on the Bobber, IMO it probably isnít what it was designed for, at least not without some mods. Luggage carrier, more comfortable seat, relaxing the OEM rear shock, maybe FC controls, etc, etc. Just about whatever you could do, itís probably been done by one or more forum members. Except, no passenger option if thatís your thing.
On the other hand, the SM, as youíve already experienced, pretty much addresses some if not all, these issues. It seems like some who have BBs, think the bikes are similar many ways (I have an original Bobber, not a BB so I canít chime in on that). Have to admit, if I didnít have my Indian Scout for longer multi-day trips, Iíd probably buy an SM since for me, the Bobber is used for day trips and around town.
Regardless of what you decide, not sure you can go wrong. Theyíre both great motorcycles. But, my concern is the dealer not letting you test ride. Thatís a big no-no in my book and might be a red flag about their customer service. If you havenít already done so, Iíd check them out more thoroughly with others whoíve bought, serviced or if possible, those who chose another dealer.