Entering Specific Text Into Cell Based On Its Format

I'm trying to make a schedule for some of my employees (300 to be exact) and I was trying to work out a way of speeding things up a bit. I've made plenty of pretty complex equations for working with the task but the solution for what I would like to do now alludes me.

Here's the challenge: I have a sheet where I would like to insert employees within row 4 and then have their shifts shown visually in the column below that, and have the hours they work put into a merged cell (or something similar), like what can be seen in the blue cell under "Employee 1" (C6). What I would like to do is just have something like a VBA detect that a series of cells is merged (red cells) and insert the corresponding time, located within B5:B33, into that cell (with same format as the blue cell). Also, above the employee's name I could put a button to run something like a macro to run the program for the corresponding employee directly under that button.

Essentially I want to merge a series of cells, hit a button, and have excel locate and input the correct times within that merged cell.