The million dollar question right there. its the without spending a bunch of money part that is relative. What is a "bunch of money"? The cost of an accident or major engine repair? or the cost of a high quality engine tune...
your choice.
Maybe do some towing first and see what things look like!
Keep your TT within your trucks rating and you should be fine.
It seems after market oil coolers can be challenging to install as the few that were available as a kit are no longer rally available.
The Crankshaft Positioning Sensor is a separate item and is not covered under any recalls. It is not installed along with the tone ring unless it sustained damage when the tone ring delaminates.
I have 2 ECU's since I have the early GED tune. The stock ECU has the tone wheel update on it. The tuned ECU does not so if I lose the tone wheel I will have to swap on the side of the road I guess. My choice but my wife rarely drives the truck.
The SKT trans tune is added/removed via the hand...