I also have 401k with 4,500 which I estimate will be 7,000 by the end of the year.Fund 1: 24kFund 2: 180k401k: 7k Right now, I am a renter that pays 900 per month, with a stay at home wife with a child on the way.

I'd also recommend staying away from townhouses if you can but understand in some markets they are more common than others.

Hi Makani, I believe that staying positive is great cash flow in itself. 

Last short term rental we put on the market was booked for a 30 day stay first day on the market.

.✅ Knowledge of Chicago Rental Laws – A good property manager stays up to date on local laws, helping you avoid costly legal mistakes.✅ Maintenance & Repairs Handled – No more emergency calls at 2 AM about a broken water heater!

Without my wife's direct involvement, I think some of our homes would have struggled to stay afloat.   

Stay away from the top 2 banks, they can take months to actually finance you and saavy agents wont accept a preapproval from them because they can take forever. 

Regarding S8, the leases are 1yr only, but S8 tenants tend to stay longer vs cash paying tenants.

I m in the same boat, doing some research and want to stay in Dubai with family, in near future. 

Airbnb with a minimum of 1 month stay could be a good reference too.