I'd also be careful assuming the market is going to cool down - depends on who wins the elections AND what the government will do in terms of pumping money into the economy (if that's the case, we could see inflation and that will not bring the prices down... 

In terms of other areas you can consider, I think Revere by the T is an attractive option, you can look at Medford (both wellington side and West side depending on your budget), Everett (West Everett is right by Wellington), and Watertown.

Have you found one site better than the other in terms of the quality of leads?

Confirm that the provider has experience with the particular investments in which you intend to invest your retirement funds as you very likely will have questions in terms of the mechanics (e.g. how do you invest in real estate, etc.).4.

But this is commercial and we are still new so I am not sure if the same rules apply in term of accepting rent in advance? 

The first thing is to set expectations with your investors in terms of the returns - while these properties are good in terms of overall returns, it takes time and effort to bring it to a stable state.

We have a toddler too, so in terms of location looking for something in an above average school district?

In terms of lead time, you need to start looking for a property, purchase it, and complete whatever strategy you are doing while you are working. 

You may wish to confirm that the new 401k provider has experience with the particular investments in which you intend to invest your retirement funds as you very likely will have questions in terms of the mechanics (e.g. how do you invest in real estate, etc.).3.

@Ryan Guffey The market says the kitchen and the bathrooms need to very nice but in terms of cost of material paint is the winner every time.