@Ediagnostics - I would recommend reviewing the following post, which provides an overview of different techniques to use when reusing tips for dispensing tricky liquids:
The second portion of this post goes into further detail regarding how surface dispensing into empty labware, as well as reverse pipetting can be used to reuse tips for tricky dispenses. You will likely want to use a small air transport volume in either case.
I would also recommend leafing through the Hamilton Liquid Handling eBook, which provides a comprehensive overview on liquid handling techniques (surface vs jet dispensing scenarios, starting on page 35) and liquid class parameters (such as stop back flow rate).
Hope this provides additional help.
-Nick