I run a large group of independent landlords and we share lots of stories and info exchanges about working with contractors.

You can learn to do this independently or get a rockstar REALTOR to lead the way.

I am not an agent but I do run a very large group of independent landlords so feel free to reach out to get connected to good sources.

Each owner has to hire them independently, so risk is limited. 

The big guys like Perma Seal and US Waterproofing always seem to be more expensive and have longer lead time but you can count on their quality until you get a more independent guy that has flexibility and is typically cheaper.   

This is a grind for sure, but you will thank your future self 5 years down the road when you actually have control of your time (which essentially is the reason people seek financial independence). 

Motive: build financial independence.

It is in the Historic NE which the farther East you go along the Independence Ave it starts to decline.

I think you should first have an independent inspection of the property done.

If the cosmetics thing continues to be an issue when we tour properties together, I am considering buying a 'rental-rehab BRRR' house (like the one I mentioned at the top of this post) using my above criteria with my independent investment money, fixing it by the time our lease is up in August, leasing half of it, and trying to convince him to move into it instead of re-renting the condo for $1500/mo.