We are currently renting our row house in Philadelphia which we purchased back in 2011 and are looking to take our investment strategies to the next level.

I do not play at this level yet, but are lenders typically OK with the owner financing aspect outlined in this deal?

That level/quality of tenant is not trustworthy enough to use any other method and you are wise to be checking the property every two weeks.

You'll think it was too late coming and it will be years before you get the perspective that it's still ahead of many of the other people at your level-You'll finally learn to dress well when you're 36.

I hope to be at your level!...

Would you say that holds true in this space, or is there a way to keep the discussion on the level of cap rate discounts and/or rehab costs with a multiplier (1.5x or 2x?)

Some, I pursued early and failed or succeeded on a small level. 

The lender will factor the experience level and the size of the project into the equation.

Also, Bend is having growth pains, with skyrocketing housing prices, that may prevent much entry-level investing soon.  

You'll find going for your first sale will slow down your training on other things, a reasonably stable yearly income level normally takes 18-24 months IMHO, becoming really good could take the rest of your life....