The $50k should be enough to cover 20% down, closing costs and minor repairs with a small amount left.

I also have a roommate and between the two my mortgage is covered.

I’ve been successfully house hacking for the past year, renting out my three spare bedrooms and occupying the fourth, allowing me to live for free since the rent covers my mortgage and utilities.

If you can get a DIL and the value is there, the BPO checks out, and your at a great enough spread and have $5k into it, I would consider owner financing it to someone like an investor or maybe a land contract if available, with enough down to cover your cost.Then you have your money back and their payments are gravy. 

If the income from the property would cover the seller finance note and still leave you some cash flow you could take out a personal loan for like 20k, give him 10% down and hold the rest for reserves.

This isn't all that interesting other than it's potential implications I will cover below.4.

That being said, the new goal is to find a SFH that can cover the mortgage while I save for more properties and ultimately provide positive cash flow when I decide to move out in the future.

Just make sure you have money in reserves to cover a few months of vacancy as well as any large repairs. 

I did some research online to see who should cover this and found mixed opinions.

I am doing it all in the first year, so that if they break this lease and move out in year 2 I have already covered the lump payment I received.How would you approach this?