However, if the maintenance issue is an bigger one, I usually need to make several trips: Check it out myself first, meet someone to get an estimate, check progress of work if it is over multiple days, review final work, etc. prior to paying for the services.

But I thought the purpose of Cap Rate was to use as an evaluation of a possible purchase.  

But, when dealing with a "historic" home, I would probably err on the side of caution and evaluate the potential needs for each individually. 

Ive had a few borrowers with properties up there that were evaluated.

But flips are a different beast so I'm evaluating my options and flipping is just one of them.

There is some serious investment knowledge being shared here.I'm from Houston and currently invest in single family homes in my area, but as I progress in experience and cash, I would like to go full steam into commercial retail strip centers. 

They will likely come out and have someone evaluate.   4.  

I'm constantly evaluating new markets.Please tell me what market you are currently focused on and why.What current trends are you seeing? 

It would be cool to see the progress and challenges. 

I have a house that I looking at buying that needs to evaluated so I can determine the cost of repairs and labor.