I have an old cast iron Craftsman drill press I have moved several times by myself. It is too heavy for me to lift but I can walk it out of the shop by tilting it and pivoting the base and I can tilt it into the bed of my truck. I transported it horizontal.
I brought my ~500 lb SawStop PCS home on a trailer (didn't have a truck then) and slid it out of the trailer. I slid it on the pallet it came on and then slid it over to a mobile base I made for it. I had to move it back and forth a couple times to modify the base. I did this before attaching the side tables, however, so I was not dealing with the entire weight.
I brought my bandsaw home in the bed of my pickup. It weighs about 250 lbs. Again I slid it out and walked it into the shop. Was easier than I thought (I had my son's engine hoist there as a backup but didn't use it).
Most recently I moved a new double oven from my garage into the house and then up into the cabinet by myself. It is also about 250 lbs. I pulled the doors to make it lighter.
You can do a lot by sliding and pivoting. But it is best to let the new owner decide what they can do. I don't think a drill press is a big deal but a 500 lb jointer needs about 4 pretty strong guys to lift or some equipment IMHO.
For a local move a truck with a lift gate is cheaper then a drop deck trailer. Give the dp buyer a old tire, with no wheel, for padding if you have one. Makes you seem like a thoughful guy and gets junk off your property.
Bill D
I've bought and sold my share of equipment, some more than 1500 lbs. I have always bought as-in where-is. Some sellers will not even help load as they want no liability if things go wrong. I have sold many machines too and always sold as-in where-is. I would not consider moving for the buyer