How low below the asking price is to low to offer?

[Benjamin Zwiebel]

TL;DR: I want to offer on a few properties but the number that works for is well be low asking price. Like 30% lower than asking. Other than the risk of rejection is there any down side to offering? 

My market is pretty rough. My city is only 7000 permanent residents and then a few thousand other transient oilfield workers. The entire economy is tied to oil and gas, which means that when times are good rents are high and vacancy is low and then suddenly it can go bad for years. So, with that in mind, when I have been running my numbers for rentals I have been doing the math using exclusively bust time rental prices, to make sure I can survive the bad times. The problem is, is that for some reason that I don't understand, property prices here are exceptionally high whether the town is booming or busting. Because the town is very small, it also means there is very few opportunists as properties don't change hands often and 95% of the town is a mix of single family homes and low income apartments. So, I have found few properties and in order to make them work, with any kind of positive cash flow, I have to offer WAY below asking price. 

For example, there is a triplex for sale of 3, 1 bed 1 bath units. They will rent for approximately $500 per month in bust times. The asking price for the triplex is $165,000 and it has been on the market for 6 months. Doing the math at the asking price with all 3 units rented, this property will cash flow negative -$5.59 per month. In order to get to a meager $150 a month in positive cash flow, I cannot afford to offer more than $128,000. This is obviously $37,000 (or 22%) below asking price. Is this an offer worth making? Getting my offer rejected will not hurt my feelings, but is there an down side to offering this low that I am not seeing? 

Thanks in advance.