Big Picture + Cash or Loan

[Eric J.]

I'm brand new to investing, so I'd like some feedback on my ideas of getting started. I'm 53. I've been teaching abroad for 20 years. I keep hearing and reading about how important it is to keep one's big-picture goals in mind, so here's my dream:

I have dreams of being employed half time, or not at all, so that I can do some serious volunteer work, spend extended periods (2-3 month/year) with family in the USA, and explore some freelance and entrepreneurial endeavors without having to worry about meeting basic expenses. I'd need only about a $1,400/month cash flow (adjusted for inflation in 2018 dollars) to meet my basic expenses, as I'd like to spend most of the year in cheap places like Colombia or Bali. 

I'm considering a real estate investment to help me meet that goal. I recently got my hopes up when a local agent told me I could possibly get $1300-$1500 cash flow on a $300k CASH investment (a 6% ROI not including appreciation). But that same agent is recommending townhomes between $250-275K, but the ROI's are coming in at just 4.5% or $1000/month. So that's not meeting my target. I have some index funds that I could cash out to increase my initial investment, but I don't believe it's smart to have everything in real estate. (but maybe that's not so important if I have + cash flow?)

This same agent introduced me to the idea of "leveraging" so that I borrow against my first investment buy a 2nd and even 3rd property, increasing my cash flow (after 10 years) to $3000-$4500 per month. I would feel super rich with this income in retirement after living frugally my whole life.

Big Question #1: Does real estate investing seem like a logical path towards meeting my goals?

Big Question #2: Does it make sense to put 75% of my assets in a cash sale and own my first rental property outright , or would it be better to postpone my dream, get a "real" job in order to be eligible for a loan, and not put most of my cash in real estate.

Big Question #3: How do I find a financial advisor who can watch out for my interests, if the financial people want to sell me their products, and the real estate people want to sell me theirs.