Been there, done that sort of. Went from single axle to tag axle to twin screw to single axle semi to twin screw 18 wheeler. It seems decent tandems are premium priced. I'd suggest learning from others experience and looking around at small semi's and skip the 10 wheeler phase.

edit:  I know, there is a reluctance to go from a good ol' farm truck to a small semi. I fought it for years and was WRONG.  Especially if you get an automatic, it is much easier to get around than a straight truck.  The only real trick is learning to back.

I'll see if I can add a few photos of my journey through trucks.

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IMGP0105 (Small).JPG (99KB - 1038 downloads)

DSCF0097 (Small).JPG (52KB - 1160 downloads)

100_9801 (Small).JPG (57KB - 1097 downloads)

76 right view 2_Small.JPG (79KB - 1327 downloads)

DSCF1422 (Small).JPG (59KB - 1251 downloads)

95 right cab (Small).JPG (74KB - 1285 downloads)

100_2215 (Small).JPG (60KB - 1166 downloads)

DSCF0077 (Small).JPG (51KB - 1078 downloads)

100_2406 (Small).JPG (65KB - 1161 downloads)

Image1873 (Small).jpg (59KB - 1262 downloads)

Picking up 38 ft Mauer.jpg (74KB - 1291 downloads)

IMG11889 (Small).jpg (47KB - 1360 downloads)