Couple things need to be considered here, you may not have thought about. First is the steering linkage, need to see if the Mac steering linkage will reach the motor and work when you place the motor back five inches. One thing that is needed with a larger motor is the ability to disconnect the steering from the engine when sailing, this is much more critical than when using say a 50hp, that bigger engine weighs a lot, and you don't want to have to turn it and the rudders at the same time. Especially with the motor tilted up for sailing, as the heavy motor will flop from one side to the other making steering very hard.
The controller you showed will not work on the console we have, unless you installed it at the top of the console, that would look bad and take away the mounting area for the gps. the remote key is what you need of the setup you have with a teleflex side mount controller.
adding to the transom, although some think you don't have to, would be a good idea I think. I added 3/4 marine plywood in three sections to mine, as well as some metal plates. I drilled two extra holes to mount the plywood and plates, and used a ton of 5200 to glue them in place. My transom seems stiff enough and does not flex at all.
using a jack plate will add stress to the transom, but if you could stiffen the transom up, it would give you extra space for tilt and trim.
There are trade offs when putting a larger motor on the mac, there are little problems that need to be overcome, like making sure the quick disconnect works with the larger motor, like I said this is a must when sailing and we have a larger motor. As far as the prop, I would try what you have before you start buying more props.
I'm slinging a 15 inch prop now, started with a 13. No telling what your engine needs till you try it.
here you see my 115 installed, with a few little mod's here and there it will disconnect for sailing as well as stay upright when tilted up for sailing. Does not move and the rudders swing the full lock to lock and doesn't hit the prop if the motor is tilted down. Room to get by into the cockpit is a bit tight, but can be done.