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The Herc-U-Lift Caster System was not designed to work on the DP1550, and I would not try to modify it somehow to get it to work. Drillpresses are very "top heavy" and any caster system needs to be carefully thought out.
Here's what I did to make my DP mobile yet stable. I bought one of the famous Harbor Freight Mobile Bases and assembled it to accept a 24"x24" piece of ply. Bolted the 3/4" ply to the base then bolted the DP to the ply. The end result is a very stable yet easily moveable DP.
All of us could take a lesson from the weather. It pays no attention to criticism.
I have the Jet mobile drill press stand (for my Jet DP) and am not impressed with it. It is easy enough to move but is flimsy and only has 3 wheels, causing it to rock. When I get a chance (like next time I move) I'll strengthen it and add arms to the side with levelers to stabilize it. I would look for other products if I were you. If you can weld, I could probably make some suggestions in a design.
I would try to find a place where you just don't have to move it. I only have three tools in my small shop not on wheels, the lathe, the jointer and the drill press. I have found where I need greater space around it, it is much easier to move the surrounding tools than to risk toppling the drill press.
I have no problem moving my drill press around, it hasn't even started to tip (I push from the bottom with my foot). If you have the room, Jerry is right about just sticking it up against a wall. "small space" is relative though which is why I have a mobile base
Thanks. I was figuring you were going to say it wouldn't work but I had to ask.
All good ideas and I might try and come up with something similiar to the herculift where you can have it on wheels to move and then lower it. I have a design in mind already. I might send out a few emails to the ones who have moveable bases to get suggestions.