He is here in Chicago with me, but does loans across the country. 

Welcome to BiggerPockets and the Chicago real estate community!

I'm a guy approaching middle-age, living in Chicago.

Highly suggest coming out to some of the local chicago IN-PERSON meetups! 

Rodrigues' recommendation may change this), but my next question would be, are there any cities/markets where 1 of the following are true: 1) You have family/friends that live there, 2) You travel there frequently (either for vacation, work, etc.), or 3) Somewhere else you've lived before AND know the area well?

Hey @Riley Poppell - Lincoln Park is prime time Chicago. 

This is the heart of the reason housing isn't mroe affordable, that landlords bear these types of costs every day.You could probably find cheaper labor, especially to haul away the junk, but not easily as an out of state investor. 

Also, if you're familiar with Chicago, it's your standard 6-unit building, so imagine the sidewalk surrounding it. 

One thing to bear in mind is that if you want first crack at a property offered by Networth, you have to finance thru Loans212.

And your net worth will thank you.If you still want to go ahead, you'd be better off buying a house than an apartment because, while the value of the building itself will go to 0, you'll still have the value of the land, bearing in mind that the land might actually lose value too given the depopulation and the yen depreciation.Sorry if I'm pooping a party but make sure you understand what you're getting into (which you're already doing by asking the forum) and then make the decision that's right for you according to your objectives.