You want to be set up right, so your assets are protected!

I would recommend starting on tax planning for 2024, then when it comes time to file next year you are already set up. 

My opinion is that you're approaching the NYC market with the frame of reference from another market and you're setting yourself up to fail.

I say all of this because of course you can always buy a list and start cold calling one by one, but making a real lasting connection with someone is far more valuable when real estate is about longevity.

I have a property I own outright in the Cleveland, OH area and would like to set up a HELOC on.

It's best to set expectations upfront and ensure they're going to cover all of the areas that you need to see.For inspections, while it depends on what your main goals are (e.g., price vs. quality & comprehensiveness), you can usually find plenty online.

Occasionally if we need a full set we will bid the two against each other to see who comes in cheaper.

I don't really like the cold so it may not be soon.

Is there another way to set this up when starting your LLC in the first place? 

If you know the right people you can buy in these states and set up a trustworthy management or mobile manager to help with the up keep and maintenance.