Every individual contract is different.

So he's cash flowing well on it, he's acknowledged that my situation will be different so I might need to raise rent.3) I think these are all valid questions, but the owner raised these himself too.

So making sure you are presenting yourself as credible and trustworthy, can make a huge difference in building the relationship and hearing about those off-market deals. 

My sacrifice… no haircuts and no fast food. 1 job full time, 1 full time side hustle. 0 debt at the time other than student loans.

There are a bunch of different figures associated with this decision, such as new interest rate, old interest rate, cash flow of new property etc, but I'm having a hard time getting my mind around how to analyze the decision mathematically.  

Not really any different than anything else.

If it's a larger organization, feel free to inquire about their different staff qualifications.2.

How long it takes to be financially ready is different for everyone.

We'll see real supply greater than real demand.Every local is different obviously, but I am talking in general.

Always ask yourself if there's a way to systemize the different tasks you come across.