I have a very nice duplex in a classy neighborhood, with each side having its own private, but very small back yard.

I mean i would not even go shopping unless i had the cash or financing arranged..

If this is a poorer neighborhood and he called you and he was working or mom was living there or a gaurantor I would consider it but I would not take him on, unemployed and not taking his own initiative for a job or apartment.

Try looking into zillow/Redfin and see what your potential rents you can get near the neighborhood by filtering the bedrooms/bathrooms of the intentional property that you are planning to buy.

When you know the buying process, the neighborhood, and how to find the property on your own, and are ready to buy another property: How can you avoid the 2-3% buyer commission portion going to an agent on an MLS listed property, without having to get your license and pay the costs of having a license?

We acquired the deal mostly for the lot, it’s a B class neighborhood in a growing city, on an excellent street. 

(This is already a bit ironic, because my full-time job, 50+ hours and 5-6 days a week is shopping for rates and products, so I am pretty good at it). 

Military housing is at high occupancy on-post, making various home displacements more common off-post in hotels or short term rental homes.Small multi-family homes vary in neighborhood types, but the majority of them (but not all) are in a low to middle class area, raising the chances of getting unappreciative or undesirable tenants.As I mentioned earlier, I have no properties and only watch the market for now.

I work in analytics consulting and have managed my finances and investments well by myself. 401k, investment accounts, high yield savings account, own a house in a nice neighborhood with a traditional 30-yr mortgage, etc. 

I'm looking to get some insight on reasons why this deal isn't moving if the numbers makes sense, however it's in a really challenging Southside neighborhood in Chicago.