I use one management company to manage two rental properties. They send me one 1099 every year showing the total income from both properties, but TT asks me which property the income is from. Why don't they just let me put in the total amount from the one 1099, and then later ask me what amount is from each property?
I had to waste time searching this forum for suggestions on how to handle this.
If your issue is not being able to enter the 1099-MISC as one form, you could enter the 1099-MISC on one rental/Schedule E.
Next, enter a single miscellaneous expense on that same rental (Property A) and label it "Split 1099-MISC btw two properties" or something similar that the IRS will understand to indicate that you're allocating one single 1099-MISC.
The amount of that miscellaneous expense should be matched to an income entry for Property B.
You should ask the management company to issue two separate 1099 forms, but if instead you decide to use the option suggested above, use the same reporting method (enter on the same property) and description year after year.
The IRS likes consistency.