In the current release of Crossover (9.2) what you'll need to do is go to the Configure menu in Crossover, Manage Bottles, and press the '+' button in the lower-left to create a new win98 type bottle.
Select that new bottle, click the Applications tab, Install Software. Expand the Runtime Components section and select Windows Installer 2.0 Redistributable and install that. Once that's finished press the Install Software button again, and under Unsupported Applications choose Other Application. Expand the Choose Installer File section and click Choose Installer File and pick your logbook .exe installer. You should then get the installer for your application and Crossover will complete the install and give you a shortcut icon to launch your program.
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