Inventor HSM lets you control when you want to keep the tool down by setting Maximum stay-down distance which reduces the number of retracts. This setting is located on the Linking tab.
Maximum stay-down distance
Enabling the Keep tool down check box and regenerating the toolpath operation shown below, produces the following results.
A 2D Pocket toolpath with a "short" and a "longer" stay-down distance
Remember: For 2D Contour and 2D Pocket, you have to activate the Keep tool down check box to set the Maximum stay-down distance value. For the remaining strategies, Keep tool down is always active but you can set stay-down distance to 0 to always force retracts.