However, he isn’t much of a dreamer which can often hold me back from pursuing business ventures or ideas.

It's the only way you'll get a good idea of what the market is really doing in your area, and keeps everyone competing to find the best coverage, deductibles, and premiums for your specific account.Hope this is helpful. 

Quote from @Scott Johnson: @Adrian Lammersdorf-Scioll I definitely like that idea.

However, you forgot/didn't mention the Costa del Sol, which, from an international real estate point of view (the topic here), is what matters.

Again, this topic can be discussed AT LENGTH as well so let me know if you want to go further into it.My suggestion to every new investor is to trust your instinct. 

It would be a good idea to assess your tolerance to risk and then plan something like that, but using a heloc is going to be around 9-11% in this market so to pay something off with lower interest rate to borrow more might not make much sense.

Based on how they respond you have an idea of what they are willing to do and you can now go and find that property.  

Before seasoning period ends, I want to sell to my younger brother who purchases with conventional mortgage.Is there anything wrong with this idea?  

There are some great meet ups in your area I'm sure and a lot of people at those meet ups are more than happy to chat and give ideas and answer questions.

I really like the idea of leveraging local contacts for walkthroughs and feedback.