On my 1430 the hyd oil cooling fan comes on at 100 deg F. It is rare for the temp measured at the loader control valve to exceed 150 deg. I cut the job short if it gets to 160 deg. Depending on what job it is doing, I can tell that the wheel motor oil is very hot because it gets sluggish and needs a lot of treadle for the machine to climb over objects.
You may want to consider changing your hyd oil. Does it smell different? You have a great HD small machine, but have to work within its limitations or you will have a lot of problems.
To add an oil cooler, I put it in series with the return from the loader control valve. In theory it is very simple, you just take the line off that has the returning oil to the hyd tank and put a fan forced air cooler in-between. The only real difficult part is finding which line it is.
I read how you propped your pt-180 up in the air so you didn't have to drain the oil, I don't really have that option. Perhaps I will just drain my hydraulic oil out and convert to synthetic 0W-40 for the colder temps while I am at it. While it rarely snows when its super cold , -10 to -20 occurs every year or so. Might help with cold starting too. I can probably identify the loader control valve return (one of the ~4 smaller lines going into the tank on the exhaust side I think....right where I put all my electronics of course
How many quarts of oil am I looking at swapping out?
Do you know the sizes / types of the connectors that the current lines have?