Simply, you want everything to be well lubricated, and there to be oil pressure BEFORE you attempt starting. This is what I would do.
If the oil is old, drain and refill. Use oil with a higher zinc/phosperous content like Shell Rotella T for diesels, or oil with a bottle of ZDDP added, just to cut down/avoid wear on a 'dry' engine.
Remove the sparkplugs and use marine fogging oil or Marvels Mystery oil down each cylinder. Coating each cylinder and letting it seep through the valve train/rings is a good idea.
Turn the engine over by hand, and see if there is any binding anywhere. Should be easy (fairly) with the spark plugs out. Wait overnight.
Spray again the next day.
Detach the fuel line from the pump. If engine not binding, spin the engine plugs out using the starter in short bursts no more than 15-20 seconds at a time. Wait a minute or two between tries. See if oil pressure develops, and get that oil circulating everywhere. Don't overdo it. (Make sure you have a good strong spark coming when you spin engine)
If it does had pressure, reinstall plugs. Make sure the battery is freshly charged. First fuel should not be from the tank, through the lines, or through the pump. Set up gravity line feed from container into the intake of the carb. Spray some gasoline into the bowl. Set the choke to make sure it is getting a rich enough feed to start cold and without fuel line pressure. COVER up the carb! (don't want backfires, do we?)
Attempt to start it in short spins. If it starts, try to keep it running. If it will stay running, it should be a cold idle speed high enough to keep up oil pressure. Monitor temperature and oil pressure, and valve train noise and make sure you there is water circulating properly, and no leaks, especially at the freeze plugs. Sometimes it might be better for first start to run the in and out hoses through a large bucket rather than the rad.
If everything is fine, gently run the engine a bit faster in little bursts by goosing the throttle connection as it warms. Gently does it. Might be dried deposits in the needle and seat and jets--this might free them up.
Button up the engine, and start again, same process. Get it warm and run the engine at a fast idle speed for about 20-30 minutes or so, with little blips. Shut down, drain that oil and refill with fresh oil etc, and go from there.
Anything to add to this, anyone?
