@Drew Denham , 2 cents from someone who has made all the mistakes; I wouldn't be skeptical of buying any property. I would be skeptical of the numbers, more specially proforma #'s.
If you do your homework, get actual #'s on income, expenses, repair history, demographic information, type of market, cap rate, cash flow, NOI, ROI, total ROI etc... and it meets your investment guidelines there is no skepticism involved. Its a go no go at that point!
Math the universal language, I only wish I learned to master it at a young age!
O, and just make sure your guidelines are sound :)
I'm skeptical of a single person viewing a 3 bedroom who tells me they are the only person living there, I'm skeptical of the new BMW pulling into the driveway of a lower middle class neighborhood looking to pay me 3 months up front cash if I will not run a background check because they had a "bad" divorce. I'm skeptical of the "painter" who will paint my house for 5k if I pay half upfront cash.
Skepticism isn't always a bad thing I just think you can remove it from the buying process almost completely.
Good luck.