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.

That could be your PM company if you plan to hire one. 

The best thing you can do is plan that the first year will be on the lean side.

Thirdly, financing and potentially selling later on could be challenging again with the part of the plan being on a campground. 

Even if you plan to self-manage, having a solid property management contact early on is always a good move.

I read about a 1091 exchange and if i reinvest my money into another property within 6 months then ill avoid paying the taxes on it. is this a good plan, if not do you have any other suggestions.  

So I’m trying to come up with a game plan  Conventional loans do require 25% down on an investment property.

I recently purchased a 2 unit property as owner occupied with one unit already rented out. 3 months after closing, I was laid off due to a restructure at my company, so I decided to rent out the other unit my girlfriend and I planned to live in.

We plan to share ownership of the property as I am going to invest my money into developing (building a Detached ADU in the back) and re-modeling the property so that we can collectively sell it for a profit.

No one expects you to put money down when you tell people exactly what you are planning to do and how it works.Forget what everyone told you about how wholesaling is done.