So Just to clarify a bit: I'm assuming the escalating earnest money you're referring to is much like any other project that takes draws at certain milestones?

There is no longer the pressure to hit certain "milestones" in life.Older generations see it as lack of responsibility or lack of maturity, but most millennials that I know are just as responsible (if not more so) than their parents, having witnessed the aftermath of the recession.

Short-term goal/first milestone: acquire enough rental properties to generate $2,000 in monthly cash flow after expenses.In my current situation, my wife and I are dealing with a mortgage of $74k at a 3.5% interest rate on our primary home.

Congratulations on the milestone @Brandon Hall

The law requires a milestone inspection to be performed every 10 years for each building that is three stories or more in height, beginning at the 30-year mark from the date the certificate of occupancy was issued.

One day, I will be able to do likewise.....that's my target but for now, am accummulating for buy and hold.Its inspiring to see people get to the milestone you are targeting.....Best of luck.....

-Starting out, intermediate level: LLC funding, business structure, different RE investment strategies & how to balance the mixture, working with others, growing business, milestones, timelines, etc

Just this past month, my wife and I hit our first major milestone -- 5 homes!

I agree with Brian, if I've never worked with a Contractor before there is no way I am giving them a 50% deposit.You should agree upon a Payment Schedule that pays the Contractor as the work is completed.The Payment Schedule should be broken down into Payment Milestones based upon major categories of work on the project (Demolition, Framing, Electrical Rough-in, Plumbing Rough-in, Drywall, Paint, Cabinetry, Tiling etc.).Where are you finding your Contractors? 

It really walks you through step by step and allows you to easily modify and create milestones for the future.