It has TONS of character and would be an amazing home when restored. 

The other side is that maybe you're not the best judge of character in selecting tenants!

Put it out there, see the feedback, if your only getting shady characters interested, then there you go.But, with a little bit of word of mouth from here, I bet you will get quite a few legit interested parties, willing to trade time and sweat for knowledge.  

Those 100 year old cabinets have a lot of character just like that guy talking to himself on the street.

He always pays the late fees but it is out of character for him to be late.

If you are keeping over a thousand dollars of someone's money, you need to use more than 250 characters to let them know. 

I have been doing electrical for 10 years and my boss has hired some ruff characters that had no place in the field.

If the tenant base is anything like those characters, don't walk, run!

You will learn to be a good judge of character and sniff out a problem tenant

I've been going back and for about painting my trim as I feel like it give character to my duplex but I'm not sure if my preferences are overiding what tenants are looking for.Would you mind sharing what paint color you used for the grey rooms and your roofing contractor?