I've been monitoring a particular domain that expired last week and wasn't renewed by the owner. While it's not particularly valuable, I personally wanted it and it meets the criteria that companies like Hugedomains tend to scoop up and hold for ransom.

I'm considering whether to let the domain expire and catch it with a dropcatcher or to try messaging the current owner to buy it. However, if I message the owner, they may think it's worth more than it is and renew it quickly. I'm also unsure if Hugedomains always beat individuals in the dropped domain process and if it's worth dealing with their high prices.

If the item isn't worth much, don't stress too much over it. Just make a firm offer and it'll likely be the only one the seller receives. Offer a specific amount of money and state that your offer will be valid for a week.
It's worth noting that the value of the item is often based on how many times it's been searched or looked up, which is information that you can access.

If you decide to let the domain expire and catch it with a dropcatcher, you'll be entering a competitive arena where companies like Hugedomains are known to participate aggressively. While it's true that they often scoop up valuable domains, it's not a guarantee they'll always win. As an individual, you've got a fair shot at snagging the domain, especially if you're using a reputable dropcatcher service. However, be prepared for a potentially intense bidding war, which might drive up the price.

On the other hand, if you choose to message the current owner, you risk alerting them to the domain's potential value. They might indeed renew it quickly, or worse, try to negotiate an inflated price with you. This approach requires a delicate touch, as you'll need to convey your interest without revealing your hand. You could try sending a polite, non-committal message expressing your interest in acquiring the domain, without making any concrete offers. This might give you an idea of their willingness to sell without spooking them into renewal.

Now, regarding Hugedomains' success rate in the dropped domain process, it's true they're a major player, but they're not invincible. I've seen instances where individuals have successfully outbid them or even negotiated a better price. It ultimately comes down to the domain's value, the competition, and your negotiation skills.

As for dealing with Hugedomains' high prices, it's a valid concern. They're known for their aggressive pricing strategies, which can be frustrating for individuals. If you do decide to engage with them, be prepared to negotiate firmly and know your limits. It's essential to have a clear understanding of the domain's market value and be willing to walk away if the price isn't right.
Both approaches carry risks and uncertainties. If you're willing to take a chance, letting the domain expire and using a dropcatcher might be the way to go. However, if you're confident in your negotiation skills and willing to take a more personal approach, messaging the current owner could yield a better outcome. Ultimately, it's crucial to weigh your options carefully, considering your budget, the domain's value, and your overall goals.