We use fwknop (time-based, single-packet, single ip, port knocking with gpg keys) + monkeysphere (ssh keys stored in gpg) + Google Authenticator on FreeBSD with PF enabled in addition to Security Groups on AWS.
Asana has great UX and is simply fantastic for shared task lists and projects among various people. Plus, it runs only $21/month (billed yearly) for total 5 friends/family. (If they went IPO, I'd snap up their arms off.)
Always do separate tickets for food. This prevents a Tragedy of the Commons, especially with large groups of people whom you do not know well, where there is a real possibility that their Wall Street d-bag friends order the lobster bisque, filet mignon and champagne and expect everyone else ordering a side salad to subsidize their stockbroker-but-has-a-subzero-balancesheet "lifestyle." Don't be a sucker.