Now those same props are selling for 100k ++++  ALL areas in ALL of Cleveland have doubled tripled or much more over the last 10 years.Good luck Neighborhoodscout lists Cleveland appreciation for last 10 years as 5 out of 10 which is not bad, but not great.  

This does not necessarily mean they will not sell, but if it is in BK it would need to be approved by the trustee, and depending on the type of BK they filed and the size of the unsecured creditors the trustee would only allow it to sell to the public to get the best price because - they have to make sure they get what they can for unsecured creditors AND the trustee is paid based on what is sells for, so they will want it to sell for more.

At the very least factor in loan buy down into your cash flow calculations because later on you can leverage the equity in either selling or financing.

The reason I am selling the Condo is to pay off some personal, and unexpected debts of about $18,000 to decrease my DTI to help me qualify for my Dads VA loan (they want to move to Texas), which is a 3BD 2BA single family home. 

Instead of selling the house (location is Arvada btw) thinking of turning it into MTR, no repairs needed on the house outside of backyard is kind of a jungle and needs landscaping work.

Should I be reaching out to current owners to find out if they are willing to sell their property and get more information about the property?

Yes you can sell to investors with tenant in place.

My other deal I did sub to and novated the property so I had no holding cost and I made money on the renovations and selling the 3% mortgage along with the house when rates were 7.5% I think my buddy felt threatened because he was like a little brother to me but I don’t want to ruin our relationship and handle this between us but I want to know if I have a legal leg to stand on or if it’s going to come to dude if you screw me.

I mentioned finding sellers who are not indifferent to selling, and therefore are motivated to sell.

I was renting this home then approached the owner and asked if they'd be interested in selling.