Would the light lose energy as it traveled upward (Does differently-shaped space redshift it)
Yes. You do lose energy moving light uphill, even if you have perfect emitters and collectors.
Is the answer the same if instead of gravity you used another force? (Say Earth was positively charged, and you converted negatively charged mass to energy, and back)
I don't think you can do that. Photons have no electric charge.
This is a thread where people can ask questions that they would ordinarily feel embarrassed for not knowing the answer to. The previous "stupid" questions thread is at almost 500 questions in about a month, so I think it's time for a new one.
Also, I have a new "stupid" question.