One of the possible ways to measure Adhoc testing is SessionBased Test Management. It means that you should define sessions; each of them should contain suggestions about what should be tested. Session looks like a mission, not like a Test Case. Then you split sessions between testers and they do their work. After testing done he prepare report which should contain information like this:
Session Name
Tester Name
Start Time
Duration
Test Design and Execution
Bugs investigating and Reporting
Session Setup
Test Notes
Test Areas
Risks
Bugs list
Issues list
After you have collected reports from tester you can measure their productivity, because you have enough data.
Also you can perform test planning because you can define all needed sessions (e.g 50), estimate how many sessions can be executed per day (e.g. 5), analyze how many perfect sessions you have (e.g. 70%) and you know how many testers will do this job (e.g. 7)
So, it is easy for now to estimate overall time
50 / (5 * 7 * 0.70) = 2 days
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