Work with someone who can guide you or just accept that your tuition will be paid through making some costly mistakes which is also legit if you can afford that :-) Good luck!

For example, I mention that every adult must pay a $30 application fee, pass my credit/criminal background, make a combined income of 3x the rent, and whether or not the property accepts pets.

@Yooni ChoiFor a first property, $100/month in cash flow might not be ideal, but it’s acceptable, especially with a house hack.

Even if someone in these forums were to teach you a creative financing strategy that required zero out of pocket cash and the seller was willing to accept those deal terms, you still aren’t qualified to own real estate with your current balance sheet.

My market of central OH has some isolated areas that are like this, and in those areas, its generally accepted as "the way it is" but those areas are also very desirable and "hip" so there is a give and take persey.

So, the financing party can hire an attorney, get a judgment and that judgment is acceptable for filing at the county. 

Can anyone recommend software which would accept monthly payments (from me to seller) and create proper 1099 forms for tax purposes at year end? 

You will never know the right number until you have a chance to inspect and get contractor bids, which will typically happen after an offer is accepted. 

The pay stubs can be hard copies or digital PDFs generated directly by your employer and sent via email; we cannot accept screen captures to verify income.Once your completed application materials have been received and it appears that you would meet our qualifying criteria, we would send you a link to perform a credit/criminal background check (this minor expense would be yours), and if those results come back acceptable, we would offer to proceed.

On top of that, maybe market rent is at or above what S8 is willing to accept.