However, if you intend to hold the property long-term or plan to pass it down to the next generation, you may want a smaller land value with a higher value to depreciable property since you won’t trigger a gain.

How do I contribute an encumbered property ($340K loan) to the LLC, let the LLC pay off my loan, but not trigger a 1099?

A few caveats before you pull the trigger... - They say that if the area you are in is on a waitlist vs active coverage (check the map here), you may experience slower speeds... basically from my understanding, they can slow you down vs other residential members. - I have no idea if I could transfer my Starlink RV account to a residential one when the time comes.

@Michael Windsor,I have done quite a bit of research in the past for Marco STRs and had a good opportunity in 2020 that I didn't pull the trigger on.  

A title transfer would likely trigger an immediate default/foreclosure.

The issue is that I am planning to buy the property under a new single-member LLC that would also be treated as a disregarded entity for tax purposes (let's call the new one Wall Street LLC).If the ownership of Wall Street LLC and Main Street LLC are exactly the same (both 100% owned by me, the sole member), does the sheer use of two different LLCs risk triggering any tax obligations or breaching the 1031 code?

The whole point is keep the original financing in tact without triggering the on due clause from the bank.

That's why I'm nervous about pulling the trigger. 

As for me, im still going to network, keep the powder dry, and pull the trigger when something comes my way that makes sense.

I am comfortable with the springing recourse triggers in most loan documents forms.