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 - 998 downloads)

DSCF0097 (Small).JPG (52KB - 1122 downloads)

100_9801 (Small).JPG (57KB - 1056 downloads)

76 right view 2_Small.JPG (79KB - 1290 downloads)

DSCF1422 (Small).JPG (59KB - 1212 downloads)

95 right cab (Small).JPG (74KB - 1250 downloads)

100_2215 (Small).JPG (60KB - 1126 downloads)

DSCF0077 (Small).JPG (51KB - 1041 downloads)

100_2406 (Small).JPG (65KB - 1122 downloads)

Image1873 (Small).jpg (59KB - 1224 downloads)

Picking up 38 ft Mauer.jpg (74KB - 1252 downloads)

IMG11889 (Small).jpg (47KB - 1320 downloads)