Many neighborhoods can be reached in 20 minutes, but Sylvania would be a stretch.

Valuations may feel high, the cycle may feel stretched, but in the end, it all comes down to the work we do when first buying a property.We want to buy in areas that will remain as robust as possible, regardless of the climate, and buying them at a price that makes sense within our calculations. 

Many policies for vacant property exclude theft with the exception that some (builders risk and COC) may cover theft of “building materials” - since the AC was already installed it would be a stretch to call it building materials.Last - I bet you have ACV coverage for this type of loss which means they will depreciate for the age of the AC before paying out on a claim.If the cost of the unit is $3000 and it’s 5 to 7+ years old it would be adjusted heavily for age - maybe 50%?

That way he does not need to come up with cash out of pocket but can also stretch his capital gains out as much as possible.To make this work in my SOLO401K I need him to do at LEAST a 10 year ballon, and would prefer if he just want to carry it 20-30 years.

Picking up 9 (I assume you have a personal home mortgage) duplexes for under $100k that are renting for $1,300+ is a great way to stretch funds & build for the future.

Building a better future for my family (kids’ college, no more future debt), getting into a better home with some more space and having passive income subsidize our lifestyle (which is not lavish by any stretch).

But that stretches out my debt, and i spend more on interest.

Nothing is impossible but I would not say it’s easy by any stretch of the imagination.

Any further suggestions are helpful as we are now scrounging for cash to make this deal happen and it's a bit of a stretch! 

The south side of Chicago is where your money will stretch the most, and some areas are great investments while some right next store not so much so you really have to do your research on the neighborhoods as much as the buildings.