Thank you for the affirmation.

I get properties under market all the time because brokers know they can send something with hair on it my way and I'll buy as-as without needing anything.

To your point--"no wonder it hasn't been snatched up yet"--it seems to me that the "hair" on this deal (the problems, etc.) are excellent levers for you to be able to work directly with him to create a customized deal that works for both of you.  

That isn't to say owner occupied can't be deals, but hard for me to see four years ago they bought it, and it's not in such horrible shape they are taking a serious hair cut to wholesale prices. 

The tenant will have an affirmative defense "satisfaction and accord" , and will likely prevail on its Motion to Dismiss your complaint/petition.

Should I wait until I have another property in the cross hairs or move to be ready beforehand?

Check the filter on the furnace , could be full of dog hair .  

Once you are in the training program, and FOLLOWING IT, then I would be having lunch (or coffee) with the following folks: Mortgage brokers / bankers/ HML, appraisers, closing attorneys and any agent with a BROKERS LICENSE in your agency with 10+ years of experience and grey hair (NOT your manager/DB).

BABY WIPES (EVEN "FLUSHABLE WIPES"), FEMININE HYGIENE PRODUCTS, HAIR, KITCHEN GREASE, AND A WIDE VARIETY OF OTHER THINGS WILL CAUSE DRAIN BLOCKAGES. 

It's much harder to get a license to cut hair I assure you.Good Luck!