For me it’s the larger down payment necessary to get deals to cash flow.

I am an Executive in a life sciences company which takes the majority of my time and I have no intention of stopping that, but want to build a larger rental portfolio to have other financial / lifestyle options in 10 years. 

For example in Chicago the neighborhood andersonville is gentrified lots of million dollar + properties but Rogers Park next door is cheaper and still mixed some richer people some lower class.

If she's debt adverse you can put larger down payments, have higher cash reserves and take the conservative route.

Appfolio typically requires a minimum of 50 doors in their system.Buildium doesn't care and is a bit easier to use - albeit it does not have as many features.

In a perfect world, I'd live in the smaller unit and rent out the larger one, or maybe even run an Airbnb if the property makes senseI’m looking for a mix of cash flow and stability/appreciation.

Hi Ryan, I am not sure how urgent moving your family to a larger home is. 

The borrower didn't move forward because the rate increased due to the lower DSCR, and the borrower was receiving less cash out.This property was part of a larger portfolio that my client was considering refinancing, but wanted to test the waters with 1 property first.

Land size definitely affects value, but the impact depends on how that extra land is actually used or perceived by buyers in your specific market.If the larger lots around your subject property mainly offer more open space but don’t add much in terms of usable area like room for another structure, pool, or subdivision potential then the price difference might be minimal.

If your goal is to get into larger, more expensive properties, it may make more sense to flip and put the money to work on another flip or more profitable rental.