Although I collect more whiskey than any other beverage, I have a longstanding love with port as well. 10 & 20 year tawnies were my first exposure to port and I fell for it immediately. I used to go through a bottle of 10-year every week until I decided it was ridiculous to be spending over $100/month on port at the age of 21. Fast forward a few years and I still buy port occasionally, usually Blake Whiskers 8-year tawny from Australia. It runs about $13 around here and is "almost" as good as the 10-year tawnies from Portugal that cost $30.
Talking with a friend recently, he suggested I try some madeira too. Something like Blandy's would only run about $20 and might also fix my sweet tooth when I'm hankering.
I've enjoyed most dessert wines that I've tried. Looking for more recommendations in the sub-$30 range. Anyone got a favorite?