Evergreen,
Have you taken the time to review what you’re typing?
In one sentence alone, you say that this property will “indeed” increase in value $80K in 2 years, even though it’s a “dry” market. And then you say that you KNOW the appreciation is there.
How will value increase in a flat market, and how do you know that the appreciation is there when it hasn’t happened yet?
Add to that, you say that a year ago a property would sell for over asking price in 1 day. Now, it moves in “decent time” IF the price is right. Sounds like a cooling market to me.
Now you say that this “nervous Nelly” as you say, has dropped the price of his home down to $300K, a home supposedly worth $370ish K. Question, has it sold yet? If not, then why? If the market is as good (or flat, dry, wet, round, etc.) as you say, then either there is a BIG problem with the house, the house is still over-valued, or the market is not nearly as good as it seems to you.
Not trying to be rude on anything. Just pointing out that sometimes you say the market is good, then flat, then bad. I don’t think I’d be buying much of anything in that kind of market. 
BTW, IF you buy based purely on the possible appreciation alone, just be clear that you’re a speculator and not a real estate investor.
If you could buy a property that has went up 10% or more annually for almost 10 years, is in the best community in the city, is in high demand, and in a place where land is running out in the city and is gone in the master community, would you buy it?
Probably not, and especially not if I’m buying at today’s FMV. Historically, RE markets cannot substain a 10% or higher appreciation index for a number of years UNLESS there is a large population growth rate (along with a number of NEW housing) to go with it. Even then, it’s only good IF the area’s capital income maintains the basically the same, or better, index. If you have to have a $500/month negative cashflow just to rent the home, then the market’s wages haven’t kept up well. When it becomes much cheaper to rent than buy, markets will usually be due a price correction.
Raj