Basically this is straightforward and obvious without any need to overthink it, but I did not find anything online concisely saying as much. So if you are reading this because you are currently overthinking it, at least now there is something on the internet saying that you are, indeed, overthinking it.
Reference links:
- GRM: drill press in the passenger seat of a BMW, but no info on how to get it in or out
- GRM: older general drill press info thread
- Woodworking Talk "Transporting a Drill Press", had the most useful info incl. the "table trick" (pair of poached pix are pasted below)
Plan A: strap a spacer block to the side of the drill press head to protect the sheet metal belt cover; tip the drill press over onto a dolly; roll everything into truck bed. See pix below.
Plan B: "table trick", lift the drill press table as far as possible and swing it around 90deg; tip the drill press over until the table rests on the dolly; roll everything into truck bed.
Plan C: remove the drill press head, deal with it and the base+column separately.
"Plan A" worked for a sub-150# drill press, and probably it did not even need the spacer block to protect the belt cover. Note: it is certainly possible to injure yourself or damage property if you are not careful using this method, but it is also not too likely you could full-on kill yourself even with a DP in the 200# range. Unless you screw up, you are lifting only around half the weight of the DP at a time.
Not my pix: clever use of the drill press table and clamps+wood rather than straps:
