I have a couple agents I work with in your area and they're seeing their listings sit longer than expected along with longer rental vacancies.

We just listed a property and the photographer we use now offers 2-D and 3-D renderings which we opted for. 

Where do I start to talk with someone about investing and what would make sense on paper for me to do this deal? 

Love talking shop anytime! 

Doing well last time I talked to him.

Plumbers I've talked to won't even come out and try to clear the clog.

Your list looks good but as others mentioned it doesn't hurt to think long term and explore refi options as well.

Use a site like Propwire to find an off market home in your targetted area, if you feel inexperienced about the renovation talk to friends, coworkers, to find contractors that are trustworthy (key part) to partner with to make the fixes needed. 

Reach out if you want to talk more.

Those who make statements like an investor should always do this often don't know what they are talking about.