Once you transition one of the homes into a full time rental you will reap that benefit by filing a schedule E at the end of the year.There are a few loopholes to consider like calling one home a "Vacation/Second home" which allows you to pull out 80% LTV with a better rate. 

I currently have a full time W2 that takes up most of my time, so putting myself in a position where I can earn extra income and eventually transition away from my W2 through real estate investing is a top priority for me.

Who in my city should I contact to determine if I can legally convert my property into transitional housing?

Congratulations on the big transition into Real Estate full time, that's definitely the goal!

What strategies have worked for you when transitioning into mid to long-term rental properties?

This approach allows you to manage the property closely, benefit from homeowner loan terms, and potentially increase its value with improvements before renting it out.As you transition the townhouse to a rental, ensure the rent covers all expenses and provides a profit.

When did you transition to Quickbooks?  

Comal County Texas is in the process transitioning to Income Value Tax Appraisal. 

The fact that you've kept the same tenants for 4 years speaks to the stability of the rental income, which is key for buy-and-hold investments.Your strategy of house hacking and then moving into a rental property was a smart way to transition, and it’s clear that the live-in flip helped you build value.

When you move in two years, transition that property to a manager and then buy a house hack at your new location.