As much as like good investments and diversification from only stock, bond investing I know I would be happier without this property.  

So now, i am considering selling it and paying off the majority of my first rental (I owe about $255k so i could payoff a big chunk and pay off the rest with added payments over a year or two), or put the money into stocks and grow it from there.

You can negotiate a good deal right now, you can't negotiate stock price 

I do not plan on discontinuing my monthly contributions to my investments in the stock market, nor want to pull any money from existing investments.

Don’t have another down payment saved at the moment but have some company stocks that will vest over the next few years that could amount to another down payment.

primary residence, a farm, my life savings and stocks --- there's alot of exposure. :')I'm curious if people do LLC and pay a higher interest rate, or do personal ownership and buy an ~$1MM umbrella policy to help protect.

When the next Covid world shutdown, or stock market crash, or China and the US stop Trade and there are shortages, or if the Panama canal goes dry in a year,  etc etc. 

I've saved up about 10k from investing in stocks and working.

It appears that market folks (bond, stock, real estate, really all market participants) just keep receiving spooky inflationary signals, which are in turn propping up bond yields and mortgage interest rates.

It is a bigger issue in the city because the housing stock is older and that means more lead paint.