Even with this discrepancy, I'm only bringing in $5/mo and will go negative for any required maintenance (which has been ~$1k-$2k a year).

Since you would be purchasing a block of five, you would receive a discounted management fee of 8% each thus the discrepancy found in your monthly net income for five versus individual purchases.

Usually Zillow and Trulia pulls their data from the county sites, but occasionally there is a discrepancy.  

There was a discrepancy in the age of the building as stated in the OM vs. what the property manager had mentioned during the meeting.

They may note a discrepancy between the actual size and the size in the assessors records, but the price should be based on the actual size, not the assessors records.

I've been asking more questions about the properties, specifically about some discrepancies with the numbers, and the broker I've been using has been somewhat hinting at the fact that nitpicking every little detail is more in the due diligence phase than the initial intro phase.Of course I understand he wants me to make an offer so he doesn't feel like he's wasting his time and there is some money on the horizon for his work thus far, but I'm kind of stuck as to how to proceed.

I am seeing this discrepancy on nearly every property I look at on every different site I research on.

If there is a huge discrepancy then it may effect your total loan amount but for the most part this will be a non issue. 

That explains the discrepancy and I'll consider myself educated!

Forgot to mention in the fine print of their disclaimers that you sign it will usually say if a discrepancy exists then the total damages will be the return of the inspection fee.