Chicago is losing housing stock at an alarming rate. 

Most investors make the same rookie mistake: They focus on problems instead of people.
Telling sellers everything wrong with their house and justifying your offer with repair costs doesn’t build trust—it kills it.
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Instead of losing 55k they will probably only end up losing $25,000 - $30,000 What made you interested in investing in this type of deal?

I'm okay with a high interest rate up to 15% because I can still breakeven on the mortgage but not sure how to finance this deal without losing my initial payments

Instead of losing 55k they will probably only end up losing $25,000 - $30,000Long term its not a great cash flow property but with some renovations and addition of a parking slab I think long term appreciation is the big goal here.

I am not quite in that boat of disposable income that I could stomach losing, but I have determined a reasonable strategy of maybe going in 1k at a time on a 3-6 month journey to 10x 5 to 10 transactions.

Do you have any advice on particular sites to look into to find tenants like this needing placement?

I have been lurking on the site and attended webinars for a while but I am just here to learn and I am soaking it all up!

I paid 2,200'on a survey and inspections of a wholesale and another heir blocked the deal 🤷🏻 You win some you lose some. 

Not the best time of year and we're in an emerging market area about an hour outside of Charlotte, NC.30Y DSCR c/o Refi's have already been done on every eligible property after rehab / 3 months seasoning.As more of our properties come up on 1+ yr of ownership, despite losing likely future appreciation of 25-30%+ annually and paying a 5% PPP, I are open to selling some houses off to start paying off much of the high interest debt accumulated outside of mortgages.