Even desperate though, this owner would literally walk away empty handed - no cash and no property.

Unfortunately, I had a bad bathroom sewer pipe problem in two separate  properties, what are the odds?

I just think for me $15000 would have been better spent on a down payment on a property.

The first mistake is the property is free and clear.  

I use Avail software and it will list your property on 10+ websites. 

He lives across the street from 2 of my properties in FL.

I wouldn't touch anything outside the urban core. if your strategy is to buy existing and old I'd recommend not to. as a newer investor depending on your liquidity look at build to rent development. building investment properties below market value by 25% and refinancing out of it to do it again. the urban core has tax abatements as well that are 15 years right now you can apply for. that means that taxes will be around $600 to $800 per year. there's cash Flow but the existing inventory market dried up a few years ago in the urban core. local realtors are going to push you to the trash areas like hilltop, south linden, etc because it's the only place numbers work. columbus is great, but remember a tenant who pays $1800 a month is different than a tenant who pays $900 a month. let me know if I can help any other way! 

I think Indy is a great diversity of communities and properties, so anything you would like should be here. 

I will be the one actively managing the property and doing most of the research, and my brother will act as more of an investor.

Why borrow against an investment property at a higher rate than you can against your primary?