You have a few options to fill the gaps in that knowledge.1. team up with a great contractor, who you can trust to not only do great work at a good price, but to teach you as they go.2. attain this knowledge yourself, reading, getting multiple bids and comparing (always a good idea, even for #1 above) - @J Scott's book on Estimating rehabs is incredible, and goes in detail on basement to roof and everything inbetween!

Are other comparable homes sitting on the market for 2-3 weeks or are they renting in days?

If you know the basics, your market, the numbers, and prices compared to rent, maybe it's time look for DEALS.

Case-Shiller index of housing shows that the Boston region up 0.48%, compared to the national index which was up 0.15%.

I love the Houston market because the barrier to entry is moderately low compared to other major metroplexes. 

Comparing renting by room versus renting as a whole what’s the yield difference?  

The only thing here is that they are in the growing pain phase where businesses are still moving to the area, but rents seem to be on the lower side compared to more populated areas in Richmond and Norfolk.  

Same could go for much of the masonry and stonework of the past compared to now.

I am in a very rural area compared to most of you so I already know or "know of" most people that want to rent from me. 

When I was in the process of purchasing the home I knew that the appraisal when I sold it would be an issue due to lack of comparable sales in the area.