It seems like a bit of money to add in to not receive back. keep in mind that in you add in a gym, you also add on a liability of being sued or tenents being injured.

He was badly injured at work last Dec 2019 so at 52 he can now live off the rents as his company let him go. 

(FYI: No one hurt, no one injured)

@Bob Floss II, I fully respect that every court and magistrate across the country are challenged with enforcing a unique and rarely-so-quickly-enacted act knowing that the everyone is injured by the events of 2020 and ultimately they are in the unenviable position of pleasing no one all of the time regardless of their ruling.Update on Toledo's specific case I observed in court with the eviction filed before March 27th yet was receiving Section 8 income:Our attorney reported that after the magistrate's reflection upon the act the ruling has been changed to "eviction granted, writ of possession to be stayed until after July 27th".

For primary residence cash out qualifiers will look into your DTI, you can cash out refi as much as you want.So to answer your questions if you pay back the HELOC you are out of cash and need to draw again if you have the cash out money its has already injured some costs so it's better IMO to deploy it to new investment.  

According to legal zoom:"For owners of rental or investment real estate, it’s common to form a limited liability company and transfer title to the property from the individual owner to the LLC.Transferring property to an LLC can limit your personal liability if someone is injured on the property and files a lawsuit against the property owner.

That sector is definitely injured.)          

In addition, you could be creating a liability for yourself if they do not- what if someone is injured or there's a car accident due to the snow not being removed- who would be liable for those damages? 

Potential liability could come up in many unexpected ways, such as a trip-and-fall or a contractor injured while on the property.

I don't need to ask, you're not insured and neither are your "helpers" so what happens when someone gets injured, say the mower hits a rock and puts an eye out.Have the owner contract to do stuff, you can pay him, or have two prices, one full of trash the other in marketable condition (marketable for you).I'd say it's a bad idea, a good thought to get cub appeal, but bad idea. :)