How do I go about raising the rents for the old tenants without getting resistance? 

However if you follow the rule of every 10 years the real estate market will correct it’s self and have cash on hand to weather the storm, you’ll be fine.

I plan to move to Colorado as I cannot take the HOT weather in Arizona and LOVE LOVE LOVE snow and experiencing four seasons.

They diversify across hundreds of properties in recession resistant and Amazon resistant asset classes.

Thanks in advance for all input.Maybe think about replacing that wooden staircase with a metal one (look online for vendors).Then you will not have to revisit this issue in the future.Also ask your insurer if there is an increase or decrease in premiums for the metal one.The ones with concrete treads are superior to the wooden treads because they don't rot and let a renter or guest fall through.The ones with the mesh metal slip resistant treads can look industrial, but might be a viable choice.And your manager is probably marking up labor for his/her General Contracting the job..

Even the difference in age may make the weathering look different for the different parts of the roof.  

Naturally you are in the worst roofing season imaginable - your good roofers are sitting on a beach enjoying the down season while the junky ones are making super low bids to try to keep their utilities on...bidding jobs that I strongly suspect aren't going to be quality work simply with the cold weather making things innately difficult.Can you patch and limp along till Spring?

If the opportunity exists to move, I would probably sell the properties while you've got a little equity and invest that money in a market that can weather a downturn.

Anecdotally, I am one of the folks that moved to Atlanta for a great job opportunity, good weather, and endless outdoor activities that Atlanta (and Georgia in general) have to offer.

Look for low property taxes/insurance, no state income tax, no destructive weather, and a live and let live attitude people are moving towards.