I solved the problem by following these steps exactly:
copy <energia directory>\hardware\tools\DSLite\DebugServer\drivers\MSP430.dll to <energia directory>\hardware\tools\msp430\bin\
edit <energia directory>\hardware\energia\msp430\boards.txt an change the 2 occurrences of rf2500 with tilib
restart energia and you should be able to upload to the MSP-EXP430G2 with MSP430G2553.
Apparently this is a known issue but there's some question about whether it's resolved using latest versions of the tool. The issue is also posted on github: