Mid city, westlake, east hollywood, south central,... these places do not improve because of the prevalence of rent control and section 8, but also because of the general incompetence of the city's administrationI'm not saying south central isn't a good investment, but it is imo highly speculative and very high maintenance, as the area is filled with bad tenants and dramas

They mean well, but often give out genuinely bad advice, which may work where they have their rentals, but not here in MA.  

A seller may tell you it's in a B class area but for that price I highly doubt it.Although Milwaukee is a great city with a lot of potential, there are many bad areas also. 

Meaning, what would have to happen for this to be a good investment (or, what could happen that would make it a bad one)? 

The time isn’t necessarily an issue but if it’s in bad shape and you weren’t expecting that or don’t want that, may be time to walk away

Bad for me at the time because they were asking me why on earth would I want to buy an investment property if I didn’t *gasp* own my primary residence?

This is not a bad thing in most cases, but something to be aware of going into the deal as you need to structure your planning around this.- Josh

He has bad credit, and outstanding debts that he needs to pay (hints the loan for 12k).

He said okay, buyer flaked, and I ended up with the property.  3 months ago today actually.The property was in bad shape.   

Here's what I want from you guys and I figured there would be a lot of pro help for this...If you were vetting my underwhelming knowledge, too make sure that I know what I'm doing as far as at least getting a deal,maybe good, but just definitely not bad, what would be your first 5 or ten questions you would ask me and would want to make sure I knew the answer yo about the deal, or general understanding before I commit to buying my first property?