seeking dessert wine pairing advice

[wondersofwine]

A German Riesling Spatlese or Auslese should pair nicely with apple or peach crisp (often have peachy notes.) At the half bottle size should be available for $20 or less. I like Tawny Port with anything with almonds and should do well with caramel ice cream but a 10-year old Tawny Port might go over your $20 figure. (My favorites are Cockburn and Niepoort but also like Sandeman.) If you are emphasizing the strawberries a Brachetto d'Acqui is a good match.