If you're planning on replicating those, the time required shouldn't be to bad. Cutting down into the deck raises the question of whether the deck is cored and how thick it is. Do you know if you're transom is hollow (inner and outer wall with air space in between), solid, or solid cored. If the deck and transom are cored, it makes cutting and glassing the hole significantly faster. Cutting 2 scuppers though cored material and then glassing the opening with at least 2 layers of bi- axial cloth and polyester would probably take 1 to 2 days. The real time will be in fairing the area and trying to reasonably match gel coat or paint. Good news is the teak is far enough away that it shouldn't be effected.
My guess is parts of 2 days to fabricate the scuppers and parts of 4 or 5 days to fair and finish. Cost will factor around actual billed time. As an example, you rough in the 2 scubbers and then seal or fair the coring. You may have to wait until the coating hardens before sanding and then applying the 2 layers of cloth. How they bill the time between steps will substantially effect your cost. My glass guy always has multiple jobs going at the same time so waiting for polyester to set up means he goes on to the next project and comes back later or the next day. In this way the job may stretch out over more days, but only cost actual working time. If you are bringing somebody into the yard for only this specific project, expect to pay more as he probably has a minimum charge per day and the clock likely is running between steps. If all the areas are solid or cored, I would guess 20 to 30 hours of actual work through final paint / gel coat. If you are cutting into void areas, the glass work will be more involved to make it solid.
Ted