Speaking with a lender is a good plan, they can help you plan for the future.  

I’ve also thought of plans for a smaller scale venue too.

You need to find people who love Costa Rica and would love to own a property there but are hesitant to buy a property on their own where they will need to manage it, and take care of it, and pay for the maintenance and any other fees associated with it.  

I would imagine most attorneys located around the MA, NH border area plan to make more than $200,000 per year.

We are looking into getting a fixer upper and plan to rent out our original residence ( Zillow says we can get $2700 median rent in our area ) while moving and fixing up the new house.

My friend and I are planning to buy an investment property (My second his first).

I plan to invest into smaller multi-family 2-5 unit turnkey properties.

The underwriter will just want to verify that you won't live in the property you are planning to purchase.

For down payment, plan to need 30-40%.

@Jacob AndersonI've only used my HELOC for investing when I have a quick exit plan.