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 - 1046 downloads)

DSCF0097 (Small).JPG (52KB - 1172 downloads)

100_9801 (Small).JPG (57KB - 1105 downloads)

76 right view 2_Small.JPG (79KB - 1337 downloads)

DSCF1422 (Small).JPG (59KB - 1263 downloads)

95 right cab (Small).JPG (74KB - 1297 downloads)

100_2215 (Small).JPG (60KB - 1174 downloads)

DSCF0077 (Small).JPG (51KB - 1087 downloads)

100_2406 (Small).JPG (65KB - 1171 downloads)

Image1873 (Small).jpg (59KB - 1273 downloads)

Picking up 38 ft Mauer.jpg (74KB - 1300 downloads)

IMG11889 (Small).jpg (47KB - 1368 downloads)