Enter "property management software" and then narrow it down to blogs or forums.

What property management software would you recommend to automate this process, not break the bank and right for a small-scale multi-family?  

@Grant Farrell, you need to submit taxes to the city showing your income and perhaps how many days you had it rented. 

We just submitted an offer for a client on a relatively turnkey 5 unit at $235k and it’ll cashflow well on day 1.Either way congrats on deciding to get started in real estate and don’t downplay the $70k you saved up for this.

Usually if you talk to an engineer in the water department and submit receipts from a professional you used to fix the problem they will do a one time credit.Whether you can offload the water onto a tenant will depend on how the tenants are conditioned in the area.

Vacant Properties Software Programs ?

I found it a bit boring, but it gave me the requirements to be able to submit my application.

My CPA has instructed me that the auto expenses (at least the proportion used for rental activities), overhead such as office supplies, software, tax preparation, and other items which occur to operate the rental properties (AS A WHOLE) are expensable on Schedule E relative to the activity (e.g. based on number of units per property) by "cost accounting or cost allocation". 

With 37 units, you don't have digital software like Buildium that can be set to automatically email a receipt?

@David Briley Sites like buildium, appfolio, etc. are management software if you didn't already know that!