But they will also up-charge for everything, which very well could make the whole project cost prohibitive.If you are willing to put in a lot of work, you might be able to tackle this on your own, and hire subs directly, but again there is A LOT of work, and being a novice, it is likely you will make some costly mistakes.  

How would I tackle this?

Then you may have enough equity/cash flow after then to tackle a 4+plex.Just my 2¢, best of luck!

Wholesaling is just like any other job you may tackle. 

I do not think you should try to tackle every problem but maybe there are a few you feel comfortable in doing and can add value and forced appreciation that way. 

I'm probably only going to tackle cosseting things myself.

I suggest that you tackle the problem that is right in front of you - you have an eviction they you want to do and need a lawyer.

From what I can tell, you need to tackle these problems as a system.

I decided to take my intermediate at best knowledge of home improvement and tackle it my self.

Working on getting a local RE lawyer and title company to tackle this.