Do you find someone on places like craigslist to get "boots on the ground" to look at the property and assess any damage?

Have you done you own personal assessment as well?  

Check for how long the current tenants have been in the property and assess the property condition.

Based on my research, in Pittsburgh, the school board tracks sales of homes and if there is a significant discrepancy between sales price/current assessment values, they will appeal and you get a higher tax bill.

Often not as much as retail centers with lots of property management but still takes work, knowledge, and skill.I have a whole process I have developed to assess risk.Hope it helps   

But if you get a 5% increase assessment, you are on the hook.  

Investigate government programs such as HUD, USDA, and FHA loans, select investment techniques such as house hacking, turnkey homes, or purchase and hold, and assess properties using tools such as Grants.gov, HUD.gov, and BiggerPockets.Good luck!

Does it have enough reserves, any special assessments on the horizon (could be extra thousands in additional fees), when is the next big expense coming (like roof change, elevator replacement, etc), the rent cap and what rents options are available.

Leveraging Ed's local market expertise, we quickly assessed the property's potential.

Leveraging Ernest's local market expertise, we quickly assessed the property's potential.