My goal is to leave stressful W2 job within 5 years or scale down to working on part-time/contract basis. 

Our software sends a reminder automatically a few days before rent is due, then it sends follow-up reminders every day they are late.

If it's possible still, it would be better for the grandmother to keep possession of the house and have the ownership transfer upon her death due to the step-up in basis the house would get.

I've spent many, many years honing my craft and I learn every day.

(Most of our cities here vary like this, and each opportunity is evaluated on a case by case basis.

However, the value of your labor generally cannot be included in the cost basis for depreciation purposes.Accelerated Depreciation: A cost segregation study would identify components of your property that can be depreciated over shorter periods, such as personal property and land improvements.

Our original and adjusted basis on each property falls in the $400s and the Cost Seg studies are being quoted in the mid-$2,000 range per property.

I'm considering taking the numbers from there (they do calculate cashflow, % vacancy, % repairs and all that) and making spreadsheets with graphs/charts so I can track everything on a property by property basis and the portfolio as a whole. 

Then you would gain the additional depreciable basis on the amount you purchased more than you sold.

I do drop down significantly, but I factor in what it would cost to run my place on a day-to-day basis and make sure not to go lower than that.