Does it make sense to invest in this market?

[Jeff Daring]

I have been trying to find properties in the Rochester, NY area off and on for the last 2-3 years.  I haven't been highly motivated, just wanting to get in the market when the right opportunity came along.  I actually do need to find a property in the next 90 days due to my work situation changing, but it seems like an almost impossible task. Lately I have been using the BiggerPockets tools to analyze deals and it seems like essentially no properties will cash flow these days in any of the B+ greater areas.  Most multi families go for above asking by 10-20% and often are cash deals.  I just want to find a property that will cash flow when I leave (currently trying to house hack).  Does it make sense to invest in say a 350k property that will cost me 200-300 a month to operate even after I move out if its in a good neighborhood?  Are people just doing the appreciation play these days?  My concern is that housing values have gone up so much lately that, like any market, the next cycle could come around and leave me in a bad situation.  My other thought is that it may just make sense to buy the property so that my monthly burden is equal to or less than it would be if I rented in the area, because at least I am paying towards my own equity.  Open to any thoughts or suggestions.