Disclaimer: I will not make any money off of this sale. I am just asking for my old boss with whom I built this company. Even though I don't work there and have no stake, I just want to solicit the best advice on her behalf. I can give more details via a PM as she doesn't want to spread the word yet.

The business is a vacation rental company located in a premier resort town in the USA. It has existed since before airbnb was even a thing. The business is very profitable and technologically self-reliant. She has spent a decent amount on technology so that there aren't multiple outsiders taking a slice of each rental. I can provide the rough numbers via PM. The SEO is already #1 in the market. The company owns its office building, and multiple vacation rentals which could be packaged in with the sale.

It is the largest vacation rental company in the local vicinity, so selling to a direct competitor doesn't seem likely. It would seem to be the ideal sale/purchase for someone who is wealthy and is looking to retire early, live in a tropical setting, make money, and still have something to do. However, maybe contacting the larger, more corporate vacation rental businesses on the mainland would be the best option?

Google searches for this are an SEO disaster which is why I am asking here. Are business brokers necessary for something like this? It is so niche that I really just don't know what to look for. Any feedback would be appreciated.

Edit: to add, it is completely turn-key. Everything could be left as it is, with all current employees. Aside from executive decisions the only thing that the owner did, since we scaled to dominate the local market, was write the ad copy because she is really good at that. She only physically spent a couple months of the year there in the last few years. The only reason she is considering selling is due to aging-out.

I have had a varied work history for the last decade but it has all been W-2. I now find myself doing consulting engagements and I am wondering if I should setup an LLC for this work. My main concern is actually limiting liability, and of course I am interested in possible tax advantages.

Has anyone else done this? If so, what’s the best way to set this up? Stripe has a program, I imagine legalzoom does as well..