Can those with experience please share their thoughts about towing with a '99 Outback, auto trans?
I've recently purchased the car and am contemplating a small vintage camping trailer too, a single axle<2000#.
Upto 2k and tongue weight up to 150 with stock springs. You could go higher on the tongue with heavier spring rates. If you are doing any hill or mountain driving, you may want to consider trailer brakes or practice with downshifting so the transmission and engine help slow it down. Install an additional transmission cooler to help with the trans temperature. Make sure your thermostat is good so you don't have engine temperature issues. Have the tires at the proper psi for the load on the car and tongue, just look at the tire information and it will give you the pressure and load rating.
The biggest issue is engine and transmission temperature issues. That car will pull a truck out of a sand pit. Been there, done that with a 99. Its the long hauls on hills you have to be concerned with. Watch the gauges.
All sounds encouraging and good advice.
I agree that an additional trans cooler is a good idea.
I'm in Illinois where everything is as flat as piss on a plate and don't intend to do any long hauls. I have great mechanical sympathy so am already a vigilant gauge watcher.