@syoung123 , the perfect solution of course is to have one each 1099--MIsc for each prop. However with some amount of extra effort you can make it work even with ONE 1099. I just tried out on my copy of Windows Home & Business and YES it does work ( with a few extra steps and careful look-see ),
I would highly recommend that you get the management company to issue one 1099 for each property -- they are getting paid for the service ( to make it easy for you and not to make easy for themselves ).
For IRS AUR program, even it gets flagged, human intervention thereafter should stop the issuance of CP2000 ( under reported income ).
Even if a CP2000 is issued , you can explain that the total amount on the 1099-misc has indeed been accounted for on Schedule-E . Plus you have the back-up data to prove your point.
Is there more I can do for you ?
