[2ndround]

Hotels are normally the easiest to hit, especially chains. A strong willed complaint of a serious nature will usually cause them to comp the room. E.g found used condom under the pillow. Free meals at hotels by complaining of food poisoning the next day. Or hit Ubereats deliveroo etc as you will have  a new address to use at each place you stay.

Hitting Airbnb usually hurts the little guy so try to avoid this.

Flights will be the most challenging to SE to be honest,  may be able to SE airline gift cards, use them to pay for the flights then refund them.

Other than this, some legitimate ways to travel for free include, house sitting, couch surfing, hitch hiking etc.

Agree that hitting individuals is not good. However with airbnb depending on the owner, claims can be covered by the insurance they have. However, I have no idea how many owners opt for that option. Heard that dealing with financial claims for owners is hassle free via airbnb insurance/coverage.

Airbnb insurance is very poor and will not cover the host in most cases that will be used to go to the end of an SE.. In addition to this, depending on the case, Airbnb can take sanctions against hosts that can go as far as a total ban from the platform, thus depriving them of their main source of income.

So please stay away of Airbnb and any others websites leaded by individuals.

Don't have experience of it myself but a buddy of mine said they quickly paid for the damage caused by the person renting.
He is a 5 star rated super host and it was his first claim so not sure how much that to do with the quick resolution.

In any chance, targetting individuals is not cool and as I said I don't know how many people have the coverage and how well it works generally.

If you own an air bnb then it could be possible to SE the coverage/insurance.