kwfiggatt, welcome. Your idea sounds interesting as I am also at the stage of grouting and have already figured out how to drill the boreholes. I suppose the easy part of it all.
The information that I gained from Vlad's grouting experience was that the problem he had with grouting was pulling up the hose that is full of grout. If you used a 1-2" tremie tube and pipe down 100ft, you must have a way to support all of that weight and also to be able to pull it up.
Vlad only went down 50-55 feet, but said he struggled with getting the tremie tube stuck and then trying to pull it up. I wanted to go down 200', but Vlad said it would be hard to grout. We discussed making a roller drum with a motor or crank to pull the tremie tube up when dispensing grout. Simular to one of these: