This comes down to personal opinions as to what is more important and cost efficient.

Can anyone recommend a window contractor in the Cleveland area who MAY be able to give us an estimate (even if just from the exterior) or knows how much (or range) it would be to replace windows in a typical 2 story brick exterior home in the University Heights area with a mid-price energy efficient window. 

RE is VERY tax efficient as is. 

Over the next 3 years the city has plans to start requiring energy efficient upgrades to all rental properties, such as low flush toilets, LED lighting, efficient heat and cooling, etc. in order to maintain your landlord permit.

I'm looking for books that are motivational, ways to create a strong routine, ways to properly manage your time while working 40+ a week, ways to work smarter, not harder, and ways to live an overall efficient and happy life. 

Advantages would be having a GC license and being in the building industry already, having a close friend or family member in the building industry, having the land to build already, any sort of experience building that would make it more efficient for you than the average person.  

Because you will be paying to construct 2 homes, I don't see a way to benefit from the efficiencies of house hacking. 

Hello - we have a small two person LLC which holds a single, small, paid-off property. We would like to move the property from the LLC to our personal names. Is there a way to do this without any adverse tax consequen...

Easy to do, very efficient.

Consult a professional, but self-repairs doesn't count as active employment and you normally can't pay yourself for your sweat equity.Pretty much what you want to do is generally ill-advised because its less tax efficient.