@Winn Cook, I would be more concerned about the future buyer's inspector.  

LOL.. but the state is really cracking down they have inspectors driving projects and checking licenses.

Great information for a nominal amount of money plus the Pest Inspector gives you guidance on what needs to be fixed for Pest 1 and Pest 2 clearance (which you will need) when you sell the home.

Now, we're not talking an 18 foot deep high dive pool down there...it might be 1" - 2" deep (but, I'm still trying to decipher the photo from my inspector and get a hold of him).It also (oddly) looks to be on top of a sheet of plastic.

I would plan on driving down there, walking through every unit with the inspector. 

Perhaps a nice 1950's built bungalow.Always hire a 3rd party property inspector to give you an unbiased feel for the home.

I visit and analyze the property, and estimate rehab costs (with experienced inspectors and contractors), add a buffer for unexpected repairs, and provide a financial model with an ROI comparison of a traditional rental vs. short-term rental.Any guidance/tips (positive comments only please) would be greatly appreciated!

If Landlord increases the rent too high, not only will the Tenant sue the Landlord, but the Town Building Inspector will also go after the Landlord.

My inspector was in the crawlspace and noted no vapor barrier or insulation under the house. 

I would talk to an experienced city building inspector to see if he is aware of any problems.