And the tenants still lived there, they had just been putting old mattresses, broken furniture, and crud there for years.

You can always start with the Simple Start subscription and upgrade if you find that it isn’t meeting your needs.  

Waiting for or getting the dreaded call that xyz was broken, flooded etc. which only happens after hours on weekend, holiday, during heat wave or snow storm. 

We're looking for more turnkey properties, or only need a few upgrades/changes.

A year ago I recently purchased my first multi family to house hack and I rant into a issue when the seller paid for a electrical upgrade to the home.

I’ve had to widen my search radius to smaller suburbs or target properties needing light cosmetic work to make the numbers work.Value-add opportunities: Adding amenities tenants love, like finished basements or upgraded kitchens, seems to justify rent premiums in this market.Navigating the competition:Be creative with financing: Seller financing or partnering with other investors has been helpful to secure deals when conventional offers didn’t cut it.Work with local agents and wholesalers: They often have their finger on the pulse of off-market opportunities, which is critical in a hot market.For those new to suburban Chicago investing, I’d say the key is finding the “sweet spot” neighborhoods—ones on the rise but not yet maxed out in price.

Is it with only the upgrade?

A mortgage lender can help determine if refinancing or tapping into equity might allow you to acquire additional properties.Consider a 1031 Exchange: If you're open to selling a current property, a 1031 exchange can defer capital gains taxes while enabling you to upgrade to a larger or more profitable asset.

At the beginning, it may be difficult to get a more expensive property that will appreciate well and so your choice is go with the cheaper property and get cash flow until you can sell and upgrade, or wait for a really good deal which you may be waiting for quite a while and its possible that you will have spent so much time waiting that you could have purchased multiple cash flowing properties by the time you get a good appreciation deal that you can qualify for / refinance after the rehab. i know anyone can go out and get seller financing deals, HML, flip to build capital or whatever the case may be I am just saying sometimes those will be harder and could result in less deals overall. 

We can start with permitting - between software upgrades / changes - reviewers that have rejected plans because of a slope in a shower on a mastered plan, the sheer volume of builds the city has been dealing with - it's been taking much longer than anticipated.