From the experts in the community, what kinds of things about this property would make you want to seriously dig in further or even pull the trigger?

This could affect your cashflow so see what kind of financing you can get.

I think everyone's situation is different, and each person's journey in discovering the kind of investor they want to be can be discovered by trial & error, or education through partnering with someone or learning through the books, podcasts or forums available to you. 

What kind of holding costs will you have for each while you fix them up and until it is able to rent?

That means you need to know what kind of financing you can get and what the terms will be. many investors hear about homeowner terms and thin they can get that because they have good credit. 

The kinds of questions you want to ask are more about the seller and why they are selling. you want information you can use to negotiate. 

As for being a landlord, knowing what kind of investor you want to be can help dictate how/ where you want to invest. 

Not wanting to portray myself as some kind of market analyst, but it is kinda fun to parrot what you hear : )

They are different kinds of risk, but both have their upsides and downsides.

There is probably an opportunity to do something in that neighborhood, the key is to identify it and decide if its the kind of work you want to be doing.