According to my projections with the boring typical 20-25% down mortgages, that should be possible in 5 years for me if hold on to my 9-5 job; quicker, if I find good partnerships, seller financing, etc (and I know I'll need that or portfolio loans once I hit 4 properties, so that may be another hurdle to overcome when I get there).So, two questions, then:1. 

@Chris Aronson Those numbers don't seem unreasonable, although from a cash flow analysis perspective you can remove your own utility bills from that number (those are resident figures and you should care about them for your personal budget, but they are not important when evaluating the property - a future tenant will pay them!).

But if you ever end up in court, the judge (and law) will say your agreement is unreasonable and it will be thrown out.You're asking if you can create a lease agreement that is reasonable, while owning rental property in a state that is unreasonable.

If you did end up in court and explained that you were going to be three days late with rent, the judge would find in your favor and you would not be kicked out.Your landlord is being unreasonable to not wait three days.

What you claim to be unreasonable is actually the normal process that all Section 8 landlords participate in. 

It sounds like part of your mental hurdle is based on what that $ can get you relative to your market.

If you can learn about these internal hurdles you may be able to build a business around it!

Are any of my assumptions unreasonable and should I re-evaluate? 

Some work around that hurdle with a hard money loan but you have to take the servicing of that additional loan into the equation of whether the deal will work or not.

If the goal is to purchase a rental property, then the biggest remaining hurdle is to determine your strategy and define what you want (and what "good" looks like).