thats always an option..

Columbus, Ohio is a great option to look into.

There are a few answers, the two most simple are (1) transactional funding and (2) options.  

Go to your favorite search engine and look for "pay rent online" to get a long list of options.

What are my options?

By utilizing social media, you can attract a more comprehensive selection of potential buyers to improve the possibility of a sale.To use social media to promote your listing, follow these tips:Create social media accounts for your real estate businessShare your listing on social media platforms like Facebook, Twitter, and InstagramUtilize paid advertising on social media to reach a targeted audience using the targeting options provided by the platformEngage with potential buyers and answer any questions they may haveRemember, social media can be a great way to promote your real estate listing and attract a more diverse selection of prospects than just buyers currently actively searching for a property.

Is house-hacking a condo in Chicago a feasible option to begin with?

I can increase my cash flow to $500-$1000 since I will need smaller loan.Other option I have is I can move into the new build and rent my existing property and cash flow $1000 a month. 

If you post your inquiry on there you should get multiple options.

Understand all of your financing options before getting into it!