Does anyone know of a good contractor (looking for a mom and pop type place) in Cleveland for some work on a triplex? 

There's different types of investing, so the question is a bit open ended. 

Does anyone have experience with this type of situation?

It does make 100% sense to avoid these types of sales pitches at the beginning :))

I have wood floors on the first floor and on the 2nd floor (including stairs) is the short industrial type carpet. 

Just type in the street address in the search field and once the map shows up click the "info" tab on the left to see details including the code enforcement cases.

Does anyone have experience with this and knows what type of contract to use, what to say to the buyer, etc.

As @Jason Bott said above you can have policies from different providers that all show the dwelling insured for $250,000 but how the company actually settles on payment (ACV or RCV) and what types of losses they will pay out for can be dramatically different. 

Does anybody know of any Architect in Tacoma who has experience in this type of development?

For you to get that type of rent, you'll wind up renting to professional roommates, and it's hit or miss, and so far for me, mostly miss.