I am interested in potentially investing in the South Side of Chicago as well.

I’d love to partner with someone and potentially go in a multi family or multi unit property!

Your best bet as to why they may be selling is simply because they are liquidating their assets, cashing out, or plan on moving onto other investments in different areas.

Repairs & Maintenance (5-8% of rental income)Take a look at the BP rental calculator to see all the potential expenses you may have while house hacking. 

Understanding the potential value of your property you can then start researching the potential for doing a HELOC & know how much you can pull out of the property to support the strategy of purchasing another home for either a flip or a rental4.

as far as financing will go for your potential buyers the duplexes will be easiest because you can get both investor and owner occupants . the multi family 5 units and more will be cinsdered commercial and cut out owner occupants . the assisted living is extremely limited when it comes to financing and now it becomes a specialty item that's an investor looking to be in assisted living business 

I'm also not in a rush to sell, I'd be perfectly happy letting the house sit for the next 6 months to a year while we see the impacts of any potential rate cuts. 

Hi Teena, I agree with Walter, and believe targeting North/Central PHX and the West valley is your safest bet.

Peace ✌🏻  You have the potential to earn more money if you do the rehab, source the contractors, determine the ARV etc.....You also have a higher risk of failure.

That’s the best bet.