or are there more advantages of transferring into an LLC and getting umbrella insurance for the LLC?

It would/could be only 15% capital gains tax and yes you could/would deduct all selling costs including commissions and transfer taxes.

Quote from @Marc Shin: I saw a video by Miles Golden and he said you change transfer your primary mortgage to a HELOC, and then you can pay all your bills out of the HELOC and pay off your mortgage in 3-12 years. 

Once I get to a point that it is making enough per month that I feel comfortable taking money out of the business that would be when I get to the point that it is worth have a specialist assist me in all deductions, credits, and future items that will help me to transfer from a W2 to working for myself fully.

If I did this, I could then transfer the land to my LLC or allow the LLC to lease the land from me for the storage facility2.

We were being transferred to that area and went up to look at a couple different homes in the area and that one came up that day, and we made a full asking offer immediately.

The only slight red flag was that they only accepted payment via Venmo or wire transfer, but that's how I accepted payment when I was selling lead bundles, so I still thought it was worth a shot.

@Kyle McVay I self-managed my first 5 units and then transferred all new units to a PM.

For instance, I served as an expert witness in a case where a property was transferred to a new owner sub-to.

Some hosts also accept bank transfers, but you’ll want to ensure payments clear well in advance of their stay.