So we went into the commercial space and pivoted to self-storage.

Trying to get her into Self Storage so I can be the paid Guru and get a free lunch from her. 

Let the tenants use curtains that are cheap and easy, plus it allows them to determine the color/decor.Tear out the sink and replace with a vanity that has more storage and an updated look.Unless this is a B or better property, I would probably leave the current mirror/vanity.

Also, especially in Near North, everyone we've had apply for the place loves that we are upfront/transparent and include parking and storage in our rental price since so many developers and larger buildings near us market the unit at one price and then when they find out it's another $300+/month for parking it's out of their budget. 

I would tell you to get really, really smart on self-storage, mobile home parks, or something that can be run by a low-skilled employee and pretty hands-off. 

If there's local boom in industry we should see the effect in immediateterm not in short tem, so what really happened in 2020-2022 is really big mistake by Fed.Also it seems very natural that in the next ten years we see lot of consolidation in the big business, much less small biz owner, and everything is owned by the conglomeration of some very powerful big names that generates cash from their operation.America is going to be more controlled by big company regardless who is in power in the goverment.So some folks are selling SFHs now in large masses to transfer into t-bills in the short period(4-8 week duration) then enter 2024 with funds to come into CRE to convert into storage, MFH(with better terms), and I think some other plays.

If you are doing 4 people, remember to add extra storage in the kitchen and to have at least 2 if not 3 prep areas (eg island and two places on the main counter) and a larger fridge.

In your shoes, you know what things cannot be changed in your life (the fact that you have debt, rent, any family situations that affect your availability). 

However, these situations can be complicated, and it's to your benefit to have a realtor on your side (if you don't already) to help you negotiate and stay within the law.Your post was pretty general, which I appreciate, but I don't know if I handled all of the concerns someone in your shoes would have.

So if I were in your shoes I would want to be really confident in the exit strategy. 1) confirm rent estimates 2) confirm ARV and the demand in that area to buy a house like that in the price range 3) are there banks willing to refinance at the LTV you want with the seasoning period you have. 40k for a house of that size that needs that work would be the cost of materials alone where we live in WI, so verify your estimates.