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You have a 3.73 or 4.10 choice in a 3/4 ton Cummins. If you plan on towing at 45-55 the 4.10 is best. If you plan on towing at 60+ the 3.73 is best fuel economy.
If you are looking at a Cummins, you aren't going to find a new body style 03-up for under $20K.
Any diesel is going to have trailer tow and heavy cooling/alternator.
People over-tow ALL THE TIME with all kinds of pickups, so if you are doing it 'occasionally' I wouldn't worry too much. Do it often? Buy the heaviest duty you can afford. I've towed a 22,000 pound tandem gooseneck quite a few times with a 2004 Chev K2500 Ext Cab Shortbox 4x4 with the Duramax/Allison with 4.10 locking diff at 75-80mph on the Interstate and it does just fine (and gets 7-10mpg)
In my humble opinion, I would buy a GM Duramax/Allison, but finding one for under $20K will be a 2001 with 150K miles.
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