Both are great markets, but CLT is hot right now, and far less expensive compared to inner Boston.

Since we will be investing remotely, we plan to work with a property management company to oversee day-to-day operations.Does this sound like a solid strategy for a first investment property?

Rent-a-plans?

Some invest in AZ with plans to live in AZ at some point.

I looked at their books at that is their actual expenses at this point.

My initial plan had been to do something like Rent-to-Retirement or REI Nation- assuming that I'd be leaving money on the table to pay for their expertise, but hoping that I would learn through the process and develop the confidence to strike out on my own later. 

Now I am considering whether to do a cash refi on the free and clear, and use a Heloc to purchase another duplex that is more expensive.  

We both run our own businesses but we feel that real estate will help make sure we both maintain our life plans of not needed to work as much any more.

Quote from @Gabrielle Cutler: HI there,That’s partly why I’m on here, I’m not quite sure the best route, especially living in the Bay Area where everything is a bit more expensive.

I'd be happy to meet you over there and give you my opinion if the foundation work and remodeling is worth the expense.