Welcome back to USMB! I doubt I can help much with questions about your Outback but you never know. I DD a 87 DL wagon and also enjoy my 2003 WRX wagon so that is what I know best.
No shame in your new car not being "new". I'll be 66 soon and have never owned a new car in my life and have no plans to ever make that mistake decision. The most I've ever spent on a vehicle was $9500 and only once have I ever bought a car from a dealer. Every other vehicle has come from a private party. The amount of money I have saved by avoiding depreciation and not being in debt constantly, has allowed me to enjoy owning multiple classic cars while on an average salary and being comfortably set up to retire at the end of this year.