I ended up hiring someone else due to a couple of unique features on my roof that he didn't specialize in.

RE agents who specialize in investors are a great source. 

I would prioritize finding an accountant who specializes in real estate taxation over one that is local.There are 20+ accountants on this message board who specialize in real estate taxation.

This is grey area (so you trade one risk for another), and I would not pursue this without consulting an experienced accountant specializing in real estate.

- Desperate or want to move in right away (besides some special circumstances such as they are from far away & have just accepted a job in the city, etc).

And of course a few of our clients are heavy into section 8 so other than the co pay  issues they are not too affected ( although specializing in section 8 is a skill set for sure).

I'd suggest hiring an attorney that specializes in property law and not tackling it yourself, but the process as a whole is quite simple.

I'm not sure of others on this forum, but off late I have explored some MOOCS such as Udemy for Real Estate education and found the "How to Analyze Multifamily Investment Opportunities" by Simon He  "phenomenal" for the price the course was offered ($9.99 a course when those specials are around and they always do).

Find a realtor who specializes in investment.

There are brokers (I specialize in them) who can handle 1-4 unit rental property loans.