Do hollow point soldering tips (and in particular, ones that can be fit to a hand soldering iron) exist?

 

The closest thing I can tink of is a desoldering iron
http://www.radioshack.com/product/index.jsp?productId=2062731
It has holloow tip, there are several types but this is the first I found.

 

I had a hollow point soldering tip once. The ironclad part had a defect and the solder got in and dissolved all the copper out of it

 

http://www.mpja.com/prodinfo.asp?number=19034+TL is an example of a deslodering unit. This is one of the least expensive temp controlled systems I've seen. If you get one, be sure to buy extra heaters and tips since MPJA has a hard time keeping them in stock.