However, when peeling back the layers I find myself at dead ends time and time again. 

With the money from my savings and stocks I have about 100k . 

Real estate is one of the best mind-sharpening exercises in the investment world simply because getting it wrong there is no stock liquidation or quick way out.

Just like bonds & stocks, different properties will have higher & lower risks.

Like any city, there is dilapidated housing stock in rough areas that can cost more to upgrade than they are worth. 

They are blaming everything on COVID but seems that hasn’t affected our dividend payments from our stocks!

Congrats getting started - advice, are you dead set on investing in NYC? 

@Seidy Lasker Wash sale rules apply to stock options if they are deemed "substantially identical" to a security sold at a loss within 30 days, such as options with similar expiration dates or strike prices.

Her team has been doing an excellent job at managing and growing my portfolio consists of core investments ( stocks & bonds) and satellite investments like gold mines, etc.

Our biggest problem is getting her out so we can do a proper rehab 60 days of dead dime waiting for her to vacate is not Ideal obviously.