A word of advice, if a tenant seems really needy/chummy in the application process that is how they will be as a neighbor.

They also have tools for on boarding investors.There are property managements softwares to help with property/asset management.There are CRMs that help with capital raising and investor automations.I would not focus on automation right now, but on the business of multifamily.

I'm sure there are other software's out there, so just select one and go with it.

I suppose that’s a better set up than Zillow but I couldn’t imagine giving possibly 40% of my hard work to a software 

Also, since you like Sherwin products, their Superpaint works pretty well for this type of application.

The city told us that all the owners of the 6 properties had to submit and sign a new subdivision application so that the city could issue permits and turn utilities on for the investors that were requesting it.

EXAMPLE: Had an applicant several years ago.

Many tax laws are open to interpretation and even an incorrect application abuse of the law is probably not getting anyone thrown in jail especially when they will eventually pay their taxes on the money. 

My understanding is that you have to submit an application with the county in the same year as the transfer/purchase.

For tasks like asset dispositions and  depreciation, you’ll need more robust tax software, or even better, the assistance of a tax professional.I’d highly recommend you not try to handle this on your own.