The massive email chain of listing automations is exhausting.

And are you leveraging any tech or automation tools for bookings, cleaning, or maintenance?

Add-on:  I do like that I can automate my late fees, no partial payments, etc.

They help automate posts and tailor content to your audience, which could definitely help speed up organic efforts.

I’m doing something similar with driving for dollars and skip tracing (recently added more automation to speed it up).

My goal is to automate the process of collecting regulations at the state/county/city/neighborhood level and create a website presenting this info in a filterable format (e.g. a map).

I ask these because if you really want to make this a long-term investment and are ready to take on the extra work (software makes it easy to automate about 80% of this, but you still need to be prepared),  then I wouldn't rush into this just to save on taxes and purchase wrong. 

Converting them into primary residences will really benefit you if you're going to hold forever.Another strategy our clients will pursue is sell those properties using 1031 exchanges and purchase passive instruments like NNN commercial properties or Delaware Statutory Trusts which will keep the depreciation recapture deferred. 

It makes their life easier and helps them automate tasks like monthly rent payments.

The process is fairly automated to insure this. - If tenant alerts us they will be late, our standard response thanks them for letting us know, but we are contractually obligated to send them a 7-Day - which they can ignore if they pay before the 7 days is up.2) We have 6 Milestone triggers when we try to contact the tenants to offer Payment Plans & Cash-for-Keys:- When 7 days is up, before we send to attorney for court date- When we receive Court Date Notice from court- When we receive Eviction Judgment after court date- When Michigan's 10-days to pay-to-stay is up- When we schedule bailiff- Day before bailiff date3) Our Payment Plans are formal, in writing and tenant MUST commit to specific Payment Dates & Amounts.