He practised the transfer from the wheelchair to the bed and the time to complete this transfer was also reassessed regularly to check his progression. cái này nghe có tự nhiên không?

@misokatsu: He practised the transfer from the wheelchair to the bed and the time taken was measured regularly to assess his progression.

The time is measured because they are certain of the value. The improvement is assessed because it is only estimated from the measured time.
Actually in speech you can use measure for both, but it doesnt sound good to repeat a word and assess is slightly more appropriate. You can just say "time taken" instead of "time taken to complete transfer" as it's obvious to the listener that you mean time taken to complete the action.