Since I have a primary home and investment home A, I am having trouble financing investment property B through a traditional mortgage. 

For instance, if you have an umbrella policy and decide to purchase a boat even if you properly insure the boat you won't necessarily have coverage from the umbrella unless you make them aware you now own a boat. 

We are Spearhead Mortgage and contact on my profile or on website. 

Your insurance agency should discuss these things with you but unfortunately many aren't properly trained or simply take orders rather than provide valuable advice... 

It’s basic, but I’ve interacted with many wholesalers that seem to get so excited about the transaction that they neglect to properly secure it.

However, we are wondering if the interest rate will likely be higher for a cash out refinance on a property we have already lived in for a year and are about to start renting than the interest rate would have been if we just got a mortgage when we first bought the property.

Quasi- creative financing with partnership 20% down and a 60/20 split (traditional mortgage/ heloc).

Older homes that lack proper maintenance are going to be poor in havoc efficiency regardless of whether they are brick or not.  

I'm a local investor, real estate broker, mortgage broker, hard money lender.

This really depends on if you are using a mortgage to finance the property.