The only hole I can poke in your plan is the ability to buy SF investment properties with only $10k in each. 

It's a labor-filled operation in a space that is already a black-hole of trust. 

There was a sump pump in the basement that was not working and the owner had a dehumidifier running and draining into the sump pump hole. 

They won't tell you to make your plan and bullet proof as possible then give it to someone whose been doing it for 20 years to shoot holes in (and believe me, they will shoot a LOT of holes in your " bullet proof" plan!). 

It's better to save up a bit longer, and start later, and jump and then find out your parachute actually has too many holes in it. 

Otherwise, are they just digging holes all over hoping to find the problem?

The success or failure of your investment depends entirely on the other condo owner, and if you have the bad luck where the other owner doesn't pay his share, declares bankruptcy, you're in a deep hole.

White collar professional that just purchased the home 3 years ago and has money burning a hole in your pocket to overpay for the finest and nicest looking everything, Tesla parked in the driveway next to a Corvette? 

This seems to be the best option in my point of view(unless a real estate CPA on here blows a hole in my hopes and dreams and tells me my gain would be taxable).

I asked her what she charged and she said she makes her money on the sale but a monetary thank you would be appreciated .