It is a specialised market that you must learn differently from SFHs.

I told her it's ok if she's not interested in doing this kind of deal, and suggested she team up with someone else in her office who specialises in what we're looking for, but she was emphatic that she still wanted to work with us.

specialised in real estate tax in Chicago / USA. 

It is highly specialised and very lucrative for those with the experience and skills to operate in that environment.For the novice you do not want to deal with that type of tenant or the government systems in place designed to protect those tenants.

@John WarrenIf you dont specialise in this segment of the market, you will be in for a big surprise!..

Hoping to work with either a small architectural firm or a single architect that specialises in small house renovations.

You might consider test marketing your area as well as speaking to realtors in your area that specialise in the rental market and determine the occupancy rate as well as the monthly rents. 

Get an expert from the specific country to assist, their are many companies (especially in europe) the specialise in land banking and the rezoning of land.

If they won't give you one, see a lawyer who specialises in evictions.

Just wondering if anybody specialises in renting  to out of town contract workers.