I rent half as a travel trailer spot and the second spot has a shop someones uses as a small car lot. 

Other people may say to shop around more, but frankly to me it's not worth the time when I'm already getting the returns and service I want and building trust. 

I've never had to orchestrate this process.Also, is it best to let your lenders know that you are shopping around to keep them a bit honest/competitive, or is it best to keep that information on the low down?

I’d shop and get your options.

The property comes with the house, 20 acres and a shop that I can run my primary business out of.

You will meet a lot of investors that, in my experience, tend to be happy to take a coffee or lunch break and talk shop.  

Did you see Sylvester Stallone moved there and is setting up shop in the CBD industry! 

@Abby Vohra there are many Facebook groups for expat relocating to Portugal that offer help in immigration, real estate and tax.Many of the ones I am a member of are British or American, but the American relocation rules are the same for you.I run one of these groups for social events in the Coimbra region.

Never really dealt with commercial tenant(s) or property. I had seen some that I may be interested in occupied as a barbershop. What are you guys thoughts on those type of tenants? -Cash paying tenants? -Steady stream...

If you're doing this a lot Amazon has a 5% cash back American Express card that is highly beneficial.