Well, this my opinion, if you like unpredictability, constant change and people/contractors with no regards to you or your property then "YES" flips and STRs are the way to go...LOL....I love it!!! 

Looking for some guidance on resources of how to begin analysis or how to build a business of this sort.

Question is, was it profitable to do all this?

Again, I believe this would hold true in most urban type markets.Let me know if that helps answer your question or if you have any follow-up questions to this.

This is the structure we were looking at which is more of a subsidiary structure and this applies to raw land development: 📌 Structuring Plan1️⃣ Set up a QOF to raise capital from investors.2️⃣ Create a QOZB to handle hotel & parking development (each separate land parcels).3️⃣ QOF owns the land & funds QOZB for development.4️⃣ Raise capital through QOF equity, bank loans, or JV partners.5️⃣ Develop the projects & operate for 10+ years for tax-free gains.

It’s exciting to hear about your plans to dive into this field, and Chicago is a fantastic market to explore once you move there.It sounds like you’re on the right track with your interest in House Hacking, Mid-Term Rentals, Short-Term Rentals, and the BRRRR strategy.

The benefit of this is that you are not paying Hard Money rates so in long term there is a lot of savings going this route.

and it doesn't work like that, especially with prices and interest rates high. 

Hi This post is old but if any one of you can share if you got lenders that can finance less than 100K?

I’m interested in connecting with him, but forgot to save the episode.Anyone know who this is?