I'm looking to get some insight on reasons why this deal isn't moving if the numbers makes sense, however it's in a really challenging Southside neighborhood in Chicago.

This could potentially help you avoid the restrictions you’re encountering with Fidelity.

Pretty frustrated and really need help ASAP - would love if someone new what I'm doing wrong or if something is wrong with the site.  

Driving for dollars and attending local real estate meetups can help you find motivated sellers and build relationships.

This will help you to determine rentable space. 

The PM is going to manage the property long-term, so they want to ensure you buy something that is in demand, we maintained, in a good neighborhood, etc.

My only intent is to help.

Lease Management - Avail.co, Apartments.com, Buildium, TenantCloud,  - many others - they can List For Rent, Schedule Showings, Provide Applications, Screen Tenants, Setup Leases, Setup and Manage Rent Payment, and other things (keep track of maintenance, keep track of expenses and make reports for accountants etc) Tenants like it because its online and makes it clear what they need to do - This also helps answer Drews question to you. - Showing a property - I have less to say on this one, looking for ideas myself.

Soon the DNS starts issuing fines to the owner, but the collateral damage to the neighborhood is already done.Abundant cash flow is a myth, especially if you invest remote, pay a PM and you are buying 100-year-old buildings with financing.

Probably worth mentioning, TurboTax can facility real-time assisting from tax professionals if needed, obviously this will be at extra cost.Hope this helps!