It is definitely a bit more tricky on an investment property, but it can for sure be done.What area of Chicago is the property in? 

We had a property with this type of sewer and replaced it with PVC, a much improved product. 

Quote from @Patrick Roberts: Angel oak and A&D mortgage are two of the bigger lenders that I know of who will do 2nd's on investment properties as of a few months ago.

I actually am working with a buyer right now that wants me to manage his house hack.  

Create a tab for each property.

I won’t pretend to be an expert by any means as I have only been at this for 4 years and have 5 properties, but I thought it could be helpful to share actual numbers and different ways to look at them.

(I.E. if one property was in both your names and you bought in just one name.

My latest vacation rental property is a charming 2-bedroom, 1-bathroom townhome located in Seattle's Queen Anne neighborhood.

If you have an actual lending strategy then different loans will serve your overall portfolio goals in different ways.

Transfer Fees or Property Tax Reassessment Some states impose a transfer tax or reset the property tax basis when property ownership is moved into an LLC.