She owns her own divorce care consulting company and assists with the "what to do's" and "how to do's" of divorce. 

Consult a local lawyer as your laws may differ from those in my state.

Just wondering if anyone has any recommendations for local roofing companies to do a consultation on what needs to be done.

Consult your own counsel.

https://turbotax.intuit.com/tax-tips/estates/the-g...You definitely need to consult an accountant.  100%.  

In case you do an assigned contract, you should still consult with an attorney before you do that, as I've heard people getting in a serious trouble doing that.

Consult those same documents to tell you how many or what percentage of homeowners need to vote for that change.If the paragraph disallowing it is in the Rules & Regulations, then you will need to petition the board to change the rules or provide you with a deferral. 

She plans to rent out 2 units while living in 1.She consulted some local architects and they came back with a ballpark of 1 - 1.5mill to complete the job with a 2-year timeline.

Always consult with your attorney before you rely on the above information.

You should probably hire a professional (lawyer or consultant of some sort) to take a look at everything and outline your options for you.