@Julie Doke: Industry specific software speaks to you and you can easily relate it to your day to day process.

We use a loan servicing software that has a monthly subscription. 

@Tamika Davis One of the biggest advantages of most software on the market is to complete these tasks you mention (maintenance, leases, rent collection, etc). 

Nathan above gave some good software recommendations, any of which would probably work well.

Quote from @Ryan Konen: You are correct that comping software like Privy, Propwire, and Propstream primarily rely on public records for their data, such as county assessor records, MLS feeds, and sometimes 3rd party aggregators.

Can anyone recommend software which would accept monthly payments (from me to seller) and create proper 1099 forms for tax purposes at year end? 

I want to structure this as concise as possible.

I still need to do a deeper dive, but the ownership structure was one of the external factors that I was thinking about.  

You will need an attorney to properly structure the partnership and you will make sure you do it correctly.

Never used software.