We planted some Mahogany and Cedar saplings. 

Added new Fencing, new water sprinkler system, new borewells, new avocado and mango saplings, fresh organic fertilizer What was the outcome?

I drove by the house last year and sure enough there are now 50 or so new sapling in the front yard. 

Realistically/Regrettably I don't see myself leaving my W2 for several more years as were just a sapling in a forest of REI.

If one's property has peeling paint, gutters with saplings growing, loose railings, majorly cracked up driveways/walks, and other slummy type characteristics it's more likely to fail. 

I cut the saplings for awhile, and now I'm spraying them with Round-up.

(Paying more for larger Trees versus saplings needing years to grow).  

I understand that you see it as your seed, but sometimes the equity would be a better seed than a possible under-performing sapling.

A friend used a jackhammer to loosen the "soil" so I could put in a sapling...Ofgift

As it happens a tree was the source of water problems we were having in my own home so I can tell you from experience you should get rid of it and maybe plant a sapling somewhere else.