Questions they will have is who is the owner, what experience do they have, is their key person insurance against them etc. 

Highly suggest coming out to some of the local chicago IN-PERSON meetups! 

Which is very complex and costly and likely warrants professional help.Now, if it's just you and your spouse, then your 2024 tax preparation is likely relatively straightforward:- you will create a Schedule C on your personal tax return- you will NOT report any costs of purchasing the property or its rehab, not in 2024- you will report your business overhead expenses such as marketing, driving, technology etc- you will end up with a business schedule showing zero income and some expenses - not breaking the rules but potentially raising an audit flagCan you do it yourself?

Figure out which best fits you and your personality and take it from there.  

I'm not a professional Tax person.

But if you see the value in investing money into your own personal education, then maybe this could be a good fit for you.

For funding, explore options like FHA loans, personal savings, or creative financing, and focus on New Jersey markets that align with your goals, such as Newark for rentals or commuter towns for house hacking.

Share what you are looking for and the deals you are working on with your network in person and on social media regularly.2.

Personally I wouldn't feel comfortable trying to wholesale a relatives $1M home knowing that I am breaking the law if I cross over into doing anything that can be considered representing them in the transaction, and knowing it will only be marketed to people who buy properties wholesale (typically investors who don't want to pay retail prices), instead of the majority of retail buyers active in the market who are typcially willing to pay more. 

Provided I can establish a solid investment plan tailored to their financial needs/comforts such as debt ratios and income, they would be more than happy to offer me some financial control.Additionally, If I wanted to, for the sake of building my own personal wealth, I admittedly have the luxury of taking a loan from my parents.