.: My first investment property happens to be my first home purchase, so my questions are hopefully basic for anyone experienced here.

NYC property values are increasing at or above the national average (4%).

Only the PMC is continuously connected with you until you sell the property.

Quote from @Robin Cornacchio: Can you use a 1031 exchange on a SDIRA owned investment property? 

You generally have to leave 25% equity in an investment property.

So, how much and whether it makes sense to update a property is about making it cash-flow better as a rental NOT ARV. 

Also when you are under contract and get condo docs, make sure to read the meeting minutes (for the past year if available) they will indicate if there are any talks of an upcoming special assessment (which you don't want).

There are several things that come into play with determining if a property sale is capital gains or ordinary income. 

Quote from @Mordecai Ese: I’m 28 and debating whether to withdraw $60K from my Roth 401(k) to help fund a new rental property.

I personally make well over $100k/yr cash flow from 21 buy-and-hold properties here.