A rental house that was larger than hers with utilities for less money than she was paying.

An appraiser would not only utilize the sales comparison approach, they would also look at the income capitalization approach.

I am an infill home builder and wholesaler in Portland, OR.We've had some great success with direct mail campaigns for single family homes.In Portland, there are many under-utilized commercial properties that currently are not at their highest and best potential, based on location and zoning.  

I hope to utilize the rent hacking approach by buying a multifamily that I can live in and rent out the remaining units.

To flip, you need to buy at discount prices fast for cash.Using the FHA to buy is great, but it is my opinion it is better utilized for longer hold times as it will take longer to get the value up enough to make a profit. 

I primarily do the fix ups and handle management, but like I said If i can make 30-50k on a filp in 3-5 months I choose that over renting out properties that will pull in 20k a year then after taxes, ins, utilities, you will clear 12-14k.I treat rentals as just a stepping stone or beginning foundation.

Or does the property have to be "put into service" before I can claim my losses. the expenses that I have accumulated for the 1 month in 2014 are property taxes, insurance, utilities and a few repairs/upgrades. 

Mortgage, taxes, utilities, and maintenance.

We have a lease that stipulates rent is $525 per month and the tenant is responsible for all utilities.  

I dont think you can if you are utilizing a third party escrow account - even in-house escrow account would hinder this.