I was able to consistently rent out a townhouse in midtown for several years to high quality tenants who could afford to pay on the higher end.

That said, @Gary Siver makes a valid point on the ease of peeling off a single glue down plank when repairs are needed.Home Depot's LifeProof brand is solid, with consistent manufacturing and a great price point.

The consistency of the cash flows coming from rentals could expedite my being able to leave my 9-5 faster, therefore focusing more time on RE, therefore building a portfolio that provides something closer to financial freedom faster. 

The purchase price is set slightly higher than market valueInterest rate on "Loan" is usually higher than bank interest rateTaxes and Insurance are paid by the buyer.All repairs/maintenance are paid by the buyer.If the buyer can't secure a mortgage by the end of the agreement, buyer will forfeit the down payment + any principal repayments.Your monthly "rent" consists only of PITI.The Seller cannot take depreciation deduction or interest expense deduction on the property as the property's title is no longer with the seller upon signing the land contract.Lease Option:The buyer pays an option fee upfront (how much is this usually?).

If you find someone that others trust via reviews, you trust due to your rapport and that keeps you consistently updated, sends photos/verification that they're doing what they say they're doing.. you're set! 

Richard there are some well priced condo s in Kahalui ,  Also some areas of the big island had housing down in the low 100s..

Have you managed multimillion dollar assets before, can you give me a track record of consistent double digit returns?

I am on Long Island, New York. 

A lawyer recommended TD for escrow accounts and working with them to open and close out these accounts is consistently fast and easy.

We have a waterfront rental on Chincoteague Island, VA.