You just keep all documentation with your files taxes in case you are ever audited.1099 requirements are another topic.

Looking for help finding simple pro forms software to analyze business model consisting of purchasing 5-10 single urban homes one at a tIme, rehabbing and renting all using line of credit and cash, the packaging in a bundle and refinancing for 5-15 year hold.

@Mark Danforth I think what confuses people about "AI" is when it failed to emerge certain people simply moved the goalposts and started calling expert systems and other sophisticated software "AI".

They promote their software and the metrics that go along with it.

In other words, everything is possible without affecting the due on sale clause.Something else to add here, I'm going overboard but since you might be having a lot of looses you want to make your return audit-proof:You must materially participate to deduct any tax losses from your airbnb activity.Use of a management firm makes material participation less likely.Use of a management firm increases the possibility that you will not be involved in day-to-day activities, and that lack of involvement will cost you any claim of investor time for material participation purposes.The IRS questions whether drive time counts for material participation purposes, and the court in Toups denied drive time as material participation time.

I'm a software developer and have worked with a bunch of REI companies that use Carrot. 

We have a software program we use for managing the units that has all our numbers in it, but I haven’t utilized anything like quickbooks yet....

Anyone using rent manager as your property management software?

I use Transunion which is built into my property management software. 

My background is in software development and web application development, so I know I can assist with technology related questions.