But it really gets serious with how you handle showings, your application, how you conduct tenant screening, credit / background checks and your communication style throughout all of this.

Hi Nick,I'm by no means an expert on South Bend, but I'm fairly familiar with it.

This is my first investment property so I feel more hesitant about going into rehab work than something fairly newer or even older but with minimal repairs/recently renovated.

But the question is whether one can actually achieve the proforma cash flow on older properties with a less economically stable tenant base.Based on your picture, you appears fairly young.My advice is buy properties in quality locations think long term 10 to 15 years - slowly and safely build your portfolio - equity and cash flow will increase over time and in 10 to 15 years you may become financially free.People talk cash flow is king but one can NOT generate financial freedom cash flow with $250,000 or $500,000 invested (equity).Even at a 10% cash on cash return, one needs $1.2M invested to generate $120K a year $10K a month.You want property to be self supporting so it needs to cash flow but once that is reached the focus in my opinion should equity growth which increases net worth.

Having two open loans for the property is not ideal as that's double closing costs but maybe that is a fairly normal strategy?

Next, maintain professional boundaries with clear communication and a strong lease agreement to set expectations upfront.Proactive maintenance is essential.

Buyers agent will still be paid, but now you have to communicate your value to your client.Jumping from one thing another isn't going to solve your issues.

Assuming your offer got accepted, the owner would need to get a unit vacated by closing (obviously this will need to be communicated).

Conner and his team have excellent communication, rented my property quickly and handle any issues thoroughly, satisfying both myself and my tenants. 

You will get your fair share of folks that have nice houses, that want to list the house and get retail.