Estimate Long-term cost of upkeep????

[Sead Osmani]

Is it possible to estimate long-term cost of upkeep, minor renovations, and maintenance of an older home?

To get an offer accepted on a 1950s home, the buyer wants us to raise our offer of 50K above appraisal. When or why would it be too risky to offer more than 50K above appraisal? If the market keeps its current pace, it will gain that value within a year, but there is a chance that it will dip and then we will owe more than it's worth. Is that a shortsighted concern?

In this scenario, is it better to go with another house that we can get for what it's currently worth, but which might have a slightly less advantageous location?