If you are shopping single family vs condo, the HOA fees for condos could take it out of the running.

We were currently spending $850/mo for a local 1000 sqft garage space that was being used for storage and shop purposes.

Which I will do now.You didn't do anything "incorrectly" I just believe you'll end up with better results this way for any insurance needs.Very difficult to shop around on your own and rate hunt. 

Much safer when more people are there, less likely for something to happen.

., etc.) without any real estate experience is a bit like trying to form and manage a law firm without any legal experience, or trying to establish and manage an auto repair shop without any automotive experience--those would be monumental challenges even locally, but doing it from hundreds of miles away is near impossible.

It can also be safer to diversify your investment properties across the country.

I would recommend that you seek out Independent Agents (that represent multiple companies) and have them shop the policy.  

The property is still shopped around to the highest bidder so it’s still being marketed.

When should I start shopping long term financing?

In the midwest where I normally shop, there are still solid deals.