Wouldn't make much sense to realize the gains and wait for the possible "dip" to play out. 

I don't want to make any enemies as this is a small market but the prices i am seeing are just way over the 1% rule and honestly don't make any sense as i run the expenses on some of these properties.

I'd like something that's relatively cost effective, so central air is likely out of the question.Does 3 zones make sense?

It does not make sense to pay mortgage interest just so that you can get a percentage of that mortgage interest back through your tax deductions. 

OK that makes lot more sense.

At the current prices for homes it just doesn't make sense to own for me.

A little hesitant on investing out of stated at this time but may have to as it a lot harder to find a deal that makes sense around here.

Properties in Wellesley and Weston are roaring high in the past decade and sometimes makes more returns than a multi-family, and it is easier to keep its value when there is financial down-turning.I understand that it is totally a personal choice based on the financial situation of a family, personal preference, and personal understanding and sense of risks/benefits with regarding to such choices.

Your question is very confusing because you claim to know what it's worth but then say you can't find anything comparable in that price range.It sounds like you are trying to justify selling this property to your tenant at a discount, which makes no sense.

So I suppose for other endeavors it makes sense.