If the loan officer won't do that for you, you've got the wrong loan officer, find a new one.

Quote from @Stuart Udis: I suspect they drew you a flow cart and then your conversations went something like this:Please kindly remove your bugs from my office

yesss you'll want to run the numbers on a few different scenarios: 1. doing a cash-out refi (new loan amount, new rate), 2. doing a HELOAN to tap into your equity... and actually, 3. selling the property and doing a 1031 into a bigger asset that will cashflow better. condos (when doing LTR) rarely cashflow much if anything. find an investor-friendly loan officer that can help you figure out which path is right for you!

I am in the process of purchasing 3 properties all right next two each other. 1 multifamily and 2 commercial office space of which we plan on using a significant portion of for our medical practice.

., home office, Wi-Fi).

I would think Chicago, as with most major cities, has strong MTR potential if the property is located near hospitals or near the office buildings in the Loop.

Some I can think of off the top of my head would be salaried sales reps, basic record of past performance, proper offering documents, back office procedures, policies and procedures for proper vetting of investor accreditation. 

Is the PM an individual that works for a larger organization or their own independent business (eg like a realtor who works with a group of people at an office)? 

They have utilized a number of financing approaches including: Minnesota Housing Finance Agency Tax Credits, Conventional, Grants through Duluth Economic Development Authority (DEDA), Duluth Housing & Redevelopment Authority (HRA) Assistance.Sharon Brown with Duluth's Life Safety office is a great resource as well when dealing with blighted properties.

They provide great education on how to properly buy and manage rent property and they have a huge physical office in your backyard.