However, my hold up is what market to look at that will help me meet my goals.

If they need to reinvest, how does sub to help them accomplish that goal?

This is where we will go back to your primary goal (Owning a cool property that you use sometimes vs. a pure investment property). 

I am guessing the beach houses were usually purchased and rented with a goal of “free” family vacations being paid for (along with mortgages) by rental income.  

Working with a mortgage broker who specializes in investor programs can be helpful for better terms as conventional loan product lenders generally don't have the best DSCR terms.More info on DSCR loans: DSCR loans won't use your income to underwrite the loan.DSCR loans are based off of down payment, credit score and either actual or market rents so it helps to supercharge an investor's real estate goals and net worth.

Once you're ready, create a goal (e.g., "I will buy at least one single-family home, duplex, triplex, or fourplex before the end of 2019") and then do it.

A different industry thought leader will present and allow a time for Q&A.The goal is to raise awareness of and encourage this strategy as well as network with likeminded investors and entrepreneurs.  

Just curious... what’s your ultimate goal for that office space..are you looking to boost resale value, or is it more about having a functional retreat above the garage?

Quote from @Jerry Zhang: I have a goal of getting 12 owner financing deals for 2025.I'm currently building a list of 1,000 multifamily agents to do monthly agent outreach to get off-market pocket listings with good creative financing terms.

It won't take long for you to zero in on what’s most important to you and aligns with your goals.