Surprised real estate doesn't play a larger role in a wealth management and legacy planning practice. 

Additionally, my partner and I are using our renovation dollars to build up cash to play in the larger 10+ unit multi-family buy hold arena.

Its usually the opposite with Canadians investing in the US and not the reverse unless its a cottage where STR may come in play for income and land development. 

Slow play.

I know NYC is very tenant friendly and I'm afraid she knows how to play the game so I don't know what to do.  

This is not investing, this is called gambling when you play for appreciation for deals like this. 

You can have great schools lots of jobs lots of fine homes in the area with no crime but the downside to all that is very high prices and little to no real cashflow .if you like little to no income and play the appreciation game ,go for it .

So, your money is not sitting in dead equity by paying off properties, and it isn’t sitting in a lousy savings account.

I need to know if the "let's buy this now and repair the property slowly as time goes on" tactic is a good plan for a value-play purchase considering all the above.

(Will leave my opinion of that fund for another time) If that is tax free or tax deferred would come into play too.Well, that's an option some people choose because it's quite safe as long as Oregon funds the pension system.