I financed this property using down payment funds from 403B and a local commercial bank.

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. 

I only spoke with one person so far and they scheduled for more information gathering/ rental investment calls from them this upcoming week.

Id have a lawyer on hand, this person seems like they will escalate issues once you notify them you aren't renewing their lease.  

This deal proved to be the perfect balance of financial gain and personal enjoyment.

. $300sqft to build at least.If you have any sort of mortgage on the property you will need an attorney to handle the mountain of paperwork the bank will give you for a lien release. 10k+, also probably some nightmare terms to have to build and sell immediately and god knows what.At this point a year has passed and you have spent at least $60,000 cash, you're about to break ground on a structure that will cost you at the very least $400,000 to build, you are still 1 year away from cashing out because you have to now build a house.

Quote from @Daniel Windingstad: Quote from @Obed Calixte: Some people have the personality, processes and systems & time to self manage, some do not.

I personally use 40% but I'm also in a higher rent area.

.✅ More Control – You’ll personally handle tenant screening, rent collection, and property upkeep, ensuring everything is done to your standards.✅ Stronger Tenant Relationships – Being involved directly allows you to build rapport with your tenants, which can lead to better communication and longer leases.Cons of Self-Managing❌ Time-Consuming – Dealing with maintenance requests, late-night emergencies, and tenant disputes can quickly become a second job.❌ Legal Risks – Chicago has strict landlord-tenant laws.

They are all under my personal name.