I have a suzuki M109R cruiser and I know what you mean aboud sitting on the tail bone position of these types of bikes. I have gotten to where I can only go about 1.5 hr on my 109 before I'm done.
Unfortunately my tail bone was still suffering on the stock Vee seat so I got a Russel Day Long and problem solved. The upright position in combo with the RDL is perfect for me.
Everyone has their opinions regarding the Wee and two-up riding. I'll just tell you that the way I ride my Vee meets my two-up demands....barely. I couldn't imagine myself being happy on the Wee riding with my girl which is 95% of the time.
2012 DL1000 Adventure (Tinkerbell)
PC-V, TRE, CR8EIX , ECM, K&N, RDL, PR4, PC-8, EB H4, WERKS, Madstad 22", 17/43 gearing, AdventureTech: Fork brace, shelf, mirror extenders, SpeedoDRD, wheel spacer, Head's-Up voltage monitor, Goldwing pegs, Sonic 1.1, Wolo Bad Boy, ExTuff Helmet Hook.