In Oregon for instance unless your doing a PUD open space cannot be required and you MUST create lots to specified zoning density.. in other words if your zoned 5k sq ft lots U cant ask for 7500 sq ft lots you must be within 10% of the base zoning.

I think I will not let him make this upgrade as a 5 year payoff would require over $100/month additional rent.  

.✔️ Your house hack is more than a 2-unit property and requires more oversight.✔️ You’d rather pay for peace of mind and legal compliance.Final ThoughtsIf you’re house hacking a small multi-unit (like a 2- or 3-flat) and are comfortable being hands-on, self-managing can be a great way to save money and learn the business.

I’m hearing they require higher down payments though.

Both turnkey properties and properties requiring minor rehab can be viable options.

When you tell them they will only get paid when the loan closes, they will disappear.If required, the only money you should ever send to the lender is for a credit check.

This is required for most landlords in the city, as part of the rental property registration program.

You will have two separate K-1s as you are each individual owners.  

It's unlikely that you'll be able to be an LOA part time as it basically requires full commitment.

I think the height requirements in Chicago are 7'6" and we're right on the edge of that.