This is a very personal question that is difficult to answer. 

Conventional would allow you to add a fence or do yard work in your bid.I cannot lend to you personally in MA but happy to answer any general questions about the 203k or other Renovation loan programs!

I was the first person to partner with them. 

I am betting your gonna find a lot more friendly amicable persons than shut doors. 

.✅ 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.

I bought this property with a private interest free loan from a friend. the person i bought it from need cash fast so i offered them a low cash offer and they accepted.I had enough money saved up to rehab the house with my savings.

Personally I prefer single family homes around that median price because that's where the most demand will be not only for owner occupants but renters as well.

We've not met in person yet, but know each other.

If you wanted to fund a portion of the down payment would you suggest a hard money lender, personal loan, etc.?

Personally, I think I would stack some cash for a year or so while I did this.