Assuming you don't have electricity, I would just pump it the 300' up the slope with a small gas engine transfer pump and perhaps a 1" line. I would probably set it up with a valve after the pump so you could drain the sap back into the tank with out losing it or having to leave it in the line to freeze.
2013-1st year...94 taps, 12x24 sugarhouse, home built evap. Gast 2065 pump with bender
2014-30x36 sugarhouse, 2.5x10 "Jutras" evaporator, 1200+ taps on vacuum, sap brothers RO. 2 sihi 2 stage pumps, 440 gal.
2015- 1000gph memtek RO, 3250 Taps, 1200 gallons
2016- Modified grimm 4'x12' evaporator with auf and aof with air preheater. Home built airtight arch front. 4250 taps?
2017- 2400gph. Lapierre RO, 10" filter press, 5000 taps