Make sure this enough gains to make it worth worrying about.

If you're not worried about current income but rather monthly cash flow, I'd recommend a 1-4 MF property.

There was no debt on the land and she lost the house so I swapped her the land and she kept the house free and clear..

I am considering getting into this space (looking at some courses), but worried that its too late, and that deep local market knowledge/understanding of buyers/connection with developers etc is required to make this work, which only incumbent/long term investors will have and would be hard for a new entrant starting from scratch to catch-up...is my hypothesis valid in your opinion ?

You get to live in a property you own for free or almost free, while learning the ropes of being a landlord and you get very very favorable financing, where you don’t have to worry about finding private lenders or getting into any complicated or exotic investment strategies on your first deal.

It's always good to invest when there is worry and uncertainty.

Once a tenant is in and they sign a year lease, there’s not too much to worry about aside from the occasional fix here and there.

Yes, I’ve got a mortgage on it now, but my cash flow went from only $1000/month to $2400/month and I picked up 3 more properties basically for free with no out of pocket cash to buy them. 

If you do a furnished LTR you will still have to worry about your furnishings and possibly consumables/linens if you plan on providing that sort of thing. 

Alternatively, I feel that a property manager could probably rent the property out and cash flow even after they take their cut, but I am worried about the screening process and potential tenants destroying my new home.