It could be more confusing in time, however you can do what works best for your clarity. Do what makes the most sense to you.
Keep good notes/records on what and why you are doing it. Both of the assets should be under the same rental activity since they are the same property. Be sur to indicate 100% rental use and Yes to rented all year since that is what is taking place now.
Set up the new asset for the 64% portion. The new roof would be added as a new asset at 36% (sounds like you already did this portion) and 64% if that's how you want to set it up.
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