For buy and holders how do you decide when to sell

[Jacob Sampson]

Looking for your decision making process.  Here is my current scenario:

I am a buy and hold guy.  I have 44 units started purchasing in 2005.  My goal is to get to 50 units then pay them off and semi retire.  That being said, this current housing market is making me wonder if I need to shift just a bit in order to take advantage of what might be a once in a decade or more scenario.

I have a 2 bed 1 bath home on a slab in a B- neighborhood that I purchased for $29k.  I will likely put about $20k into the remodel and it will likely rent for $800/month.  I have several homes and a long history in the area.  I consider this property my bread and butter.  It is the type of property I am always looking for.  Good area and solid rent to purchase/remodel price. Plus I love slabs.  With that in mind I had not entertained the idea of selling.

But my realtor came a long and after evaluating the property and current market thinks she can ask $95k.  Assuming $8k in transactions costs I clear $37k.  This seems like a no brainer to sell even if my long term goal is buy and hold.

So my question is what is your decision making process for this scenario?  Do you stick to your long term goal or is their some calculation like, if I can make 10 years worth of profit all at once then I go ahead and sell?

I appreciate the feedback.