Then transitioning toward fix and flips along with buy and hold rentals.

Starting with duplexes and transitioning into single-family homes (SFH), flips, or even commercial investments like a storage facility is a solid approach.

I assume based on the price point these are C/D locations at best but if you can point to reasons why these Sub 100K housing communities will transition to better neighborhood and appreciate then perhaps the voucher program makes sense.

After graduating college with a degree in both marketing and finance I transitioned to the lending side of the real estate industry.

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.

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. 

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.