If you want some hand-holding, Fidelity is your best choice. That's especially true if they have an office nearby. Ignore the pitches for them managing the money or selecting funds and just ask them to roll over the IRA's. You can sit down with them later, once you know what you want. If you want the usual choices recommended here, look at Fidelity's Spartan Fund series. These are very low cost index funds, similar to what Vanguard offers.
It would behoove you to fund IRA's for both of you for 2013 and 2014 if you can afford it. If your husband works in January, he can contribute up to the amount of his earned income for 2014 or $6,000, whichever is less (unless the limit is raised). Again, set those up at Fidelity or Vanguard. The rollover IRA will be a traditional IRA, you can do Roths with after tax money if you make too much for the tax deductible traditional IRA.
Where are the Calvert and Oppenheimer accounts held? That's who Fidelity or Vanguard will have to go to get the funds rolled over.
I can't really help you with the annuities. You can roll them over into an IRA, but I don't know what the costs would be or what you might lose by doing this. My personal choice would be to move them to Fidelity or Vanguard, and skip TIAA-CREF.
Looks like TIAA-CREF put you in a target date fund that charges expenses of 0.25 percent over whatever the underlying funds charge in your 403b. You can probably do better. If you post all the choices available in that plan, you will get suggestions on what to do.
With ten rental units and two pensions, I suspect you will be just fine financially. Optimizing the retirement accounts will be icing on the cake!