And when we do take over the listing, is there anything we can do at that point to make the transition smoother?

I think that down here, you will find more neighborhoods that are transitioning for the better that you can add value to and get cash flow as well as appreciation. 

Im looking to transition from agent to acquisition manager, who/ how would I go about it?

I will say, with furnished rentals, it takes time and money to fully furnish them with all the bells and whistles but it did allow me to get higher rents... only downside is, if you are out of state, it is not easy to manage remote unless you have a good property manager/company.I have personally started to transition out of STRs due to zoning/town regulations and have already unfurnished one of the apartments to turn it into a long rental for more stable residual income.

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.

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?