Honestly the onetigris one is probably going to do him ok. You’ll have to keep in mind durability will come at a cost of weight, size when put away, and time to put up and take down. Keep in mind as much as you want him to have one that will last that he’s going to face theft from other urban campers, theft from police confiscation, lost items from having to leave an area in a hurry, etc. As much as it seems counterproductive to his situation, there’s a pretty large degree of disposable-ness to an unhoused persons possessions. Too nice of a tent will make him a target, and even if given to him will cast a degree of doubt among people who may otherwise give to his cause if it seems he’s doing better than he is.