why would he entertain your lease option, when he is looking for a buyer? 

@Matthew McNeilThe BEST books on Cash Flow which tells you exactly what it is, how to use it, and why you should really study the Internal Rate of Return (IRR) and it's derivatives, is this one: What Every Real Estate Investor Needs to Know About Cash Flow..However, you will need to understand Excel Functions and how general spreadsheets work.The other issue is that the Author, Frank Gallinelli, probably makes the assumption that most of the readers of this book have at least High School Math.I will tell you from my own teaching of Adults, there is NO WAY the average American Adult, including Doctors, Lawyers, etc. remembers Math to the extent of High School.Yes, you don't need to know Pre-Calc, but people get so confused with Math.

No Evictions, EVERI also tell them there is a $35.00 non-refundable background check that THEY will pay for through SmartMove.I still end up with a wide pool to choose from...........then when I meet them...........The best qualified tenant somehow miraculously/coincidentally is the one with the least amount of adults moving in to the property...........If they have a 6 bedroom voucher and it's going to be a mother (and invariably her boyfriend) moving in along with 5 kids I'm good with that.You may want to see if your tenants "volunteer" information about having a lot of family in the area because invariably that "family" usually winds up living at the property......but if someone says they or their boyfriend does NOT have a lot or any family in the area then they seem to miraculously/coincidentally end up at the head of the line in my book as far as being best qualifed to move into my rental.

Not that I was neglecting it before, but the pressure is on because soon I will be "fully adulting."

With Chicago minimum wage @ $12/hr, assuming 2 working adults (working minimum wage), household income would be almost 5x the monthly rent for my 2BR apartments, leaving about $3k/mo for other expenses.

Again, I would not entertain any wood box around the flames!!

A good thing especially for young adults who have student debt. 

For two adults, that's $70-80 in application fees. 

I immediately reached out to my agent asking to schedule (morning after it was listed), and was told they were entertaining two, and potentially a third offer by noon.

I would imagine you would want to be pretty selective in adding a roommate as you are married and already an adult...