Low ball offers on Multi-Family; is it ok?

[Ryan Mancuso]

If a property has been on the market for a while (over 100 days) is it OK to "low ball them? 

Example. There is a duplex that has been on the market for 111 days listed at $244,900 in Prescott , AZ (about what they're going for). If I run the rental property calculator and my "home run" price is $185,000, is that too low of a price to offer? Will I gain a reputation as a lowballer? Or is it better to just offer and have them say "no?"