Welcome to the Forum from Sunny Alaska!
Small pipes? Go to smokingpipes.com and use their pipe search function, you can sort by shape, length, price,maker, finish, even bowl dimensions, it's handy. Click on the little pipe logo right by the search box at top right. Anything from Savinelli or Peterson is a good place to start. They make a huge variety, I like Savs just a bit more.
Sweet Aromatic Tobaccos that are readily available, also on smokingpipes.com (and elsewhere) in the flavors you mention:
Cherry----Cult Blood Red Moon, MacBaren 7 seas red
Vanilla-----Lane 1Q, CAO Eileens Dream, or CAO Moontrance (I think has vanilla AND bourbon?) and hundreds others (vanilla is popular)
Rum ------ Sutliff Barbados Plantation, Cornell and Diehl After hours (MacBaren Navy Flake is less sweet,not an aromatic tobacco,but you should try it eventually to branch out a bit)
Bourbon-----Cornell and Diehl Pennington Gap, CAO Moontrance
That oughta get you started! Sorry about the loss of your father and his possessions. And again, welcome to the forum.