Couple years ago, I was approached by a good friend of mine who was very interested in investment properties.

We use a cashflow approach. 

There's no right or wrong way to do it but I enjoy hearing other peoples approach.

You can never prepare fully and you will always be able to do it better, I would recommend buying your primary as a live in flip or house hack first, it is hard to mess up if you approach the purchase with just a few calculators and make sure you have some equity starting off by buying it at a discount.

My approach is reverse engineering my life.

So why do we take this approach- We can't by law in Cook County turn someone down who has a voucher.

I'm not familiar with this approach, but very curious

It will need Cap-Ex sooner or later, so BRRRR would be the ideal approach here; I'm approved for a conventional loan, but could start applying in earnest for a bank loan, or possibly pursue an option I have to partner up to make a cash offer (this deal is right around that 100k mark where my lender would only reluctantly do such a small conventional loan...another reason BRRRR is appealing).

We will provide a time and location when the date approaches and we know how many will be in attendance.

In competitive situations when you have multiple people interested, does a best and final approach work, so the tenants can offer incremental rent or term etc?