Even if things look clean I would run my carpet shampooer over it anyways to ensure it was clean for the next tenant because even a clean looking carpet can hold a lot of dirt.

Nor am I experienced in proper contracts in establishing the right paperwork to ensure legal/asset protection for both parties. 

I don't particularly like the strategy of going back to a 30 year (if that's what is being proposed) just to ensure the property "cash flows." 

Is the best person to consult on this a CPA or lawyer to ensure we get properly set up for tax considerations and values. 

They have a reputation to uphold and need to ensure they put the right amount of time and effort to it, which is fair. 

What do you do to ensure that the tenant is responsible for security deposit disputes since that is the largest reason for owner lawsuitsHow familiar are you with the newly changed laws that can affect you the owner if they are not used correctly?.

If they wish to continue living in the unit after the price increase great (be sure to screen and ensure they can afford the new amount). if not, let them know you're sorry but the arrangement isn't going to work out.

Especially at the beginning ensure your mistakes are small ones. 

My advice to you is to be sure you understand the property taxes in this state, and use the calculators to ensure your numbers will work for you.

Yes, I will ensure a contractor comes out with us when we do a second tour post-storm here.