Their reports will give you some indication on what a market is like.Next step I would do is simply visit homeaway,vrbo,airbnb and go through their regions and start compiling data you gather on each region.What Are People Charging?

Last month I went to Somerville to visit an old friend who just moved into an "Awesome new apartment"  and it's one of yours right off of Broadway. 

I'm trying to find some recommendations for an experienced contractor to visit some of these properties with my realtor and give a better idea of the type of work and cost each  might need.Any help or guidance would be much appreciated!

Some quick searches seem to indicate that the market in Oahu is somewhat unique (rules limiting short term rentals, lots of leaseholds, etc.).  

You may want to check with the local mobile home dealerships and visit a few parks in your area.

Everyone's personal preference is unique but as Thomas S. mentioned, I would never pay off a mortgage.  

Chad Clement , don't rely on pictures, go see the unit or have your agent visit it and send you pics and their assessment of what it is worth.Is this for buy and hold?

You could perhaps get a first time home buyers loan with a lower down payment...We were not super happy with the Realtor we used for our first purchase and we are now working with Micky Herzing... he is very good and also has about 40 of his own investments...If you connect with him I am sure he will have some good advice.I will send you a colleague request...we are planning to come for a visit next month, perhaps we could get a cup of coffee and discuss all things real estate!

In the beginning, do not do anything unique.  

It was less an excuse to visit the property periodically than a method to curb utility expenses.