That 5° can make a huge difference to the tortoise.Moral of the story is that even after all the caulking and weather stripping, it probably only elevated the temps by about 5-7F.
The CHE is set much too low. With a tortoise under it there will be only a few inches from the heat source to the top of the shell. It will have a very drying effect on the shell and possibly dehydrate your tortoise as well, causing additional health problems.I don't know what else to do. I do have my suspicions that the CHE is kinda set too low from the roof so it's only maybe 6-7 inches from the substrate and it only seems to be hitting one spot. Under the CHE, the substrate temp is like 120-130F which is fine and dandy but other areas are 55-65F substrate temp.
The 55°- 65° substrate in other areas away from the CHE indicate that you are losing heat through the floor. Insulating the floor, or placing the box on an insulated pad of some sort might be an easy fix for this.
A radiated heat source is definitely better for the overall health of your tortoise. It may not resolve the problem of heat loss due to lack of insulation in the bottom and top of your box. In a well sealed and insulated box of this size (not perfectly sealed) as little as 150 watts should be able to maintain 85° inside while it is 30° outside.Tomorrow is when the oil heater comes in the mail and they radiate heat as opposed to a single spot, so I *THINK* it will fix the issue.
If you continue to have problems with temperatures after installing the new oil filled heater, perhaps you can ask the person that built the box for you what it might take to insulate the top and bottom.