Thanks again, Nolan! I own the book, and I agree, its not friendly reading, and doesn’t contain any of the answers to the technical questions I had regarding entering data into the website. Thanks again for all your help 
3 rounds and 5 players is yechh. There is really no good way to do it satisfactorily without resorting to tricks.
One trick is cross-round pairings. In round 1, one player has to sit it out for a while. Then, when one of the other two games finishes, ask the players in the finished game whether either of them would like to start their next game early. If one of them volunteers to do so, immediately have him begin his game with the player who was sitting out. Consider this new game to be round 1 for the player who was sitting out, and round 2 for his opponent. With any luck, this cross-round game will finish early enough not to disrupt the schedule for the remaining players.
Then, when you pair round 2, one player has already played 2 games, so just pair the remaining four players.
Cross-round pairings work well with relatively low-rated and unrated players, as these games tend to finish quickly. They do not work well with Masters, Experts, and A players, who tend to have longer games.
Bill Smythe
Another trick is for the TD to pair himself in and out of the tournament, round by round as necessary, so there will always be an even number of players.
Bill Smythe
Thanks a lot Bill! Both great ideas. I think for now I have decided to make it a Round Robin tournament. Four rounds. The downside is that it will take longer and we likely won’t finish in one evening. But the pairing seems more fair to me, and much less messy. Everyone just plays everyone
If you post the RR table and let players find each opponent as soon as they’re available, you can usually get a RR event done a bit faster. Some players are going to use nearly all their time, but most won’t.
I’m certain Mr. Myers must realize that a round robin tournament for five players will require five rounds, not four. In a round robin tournament with an odd number of players, each and every player will have to sit out one round while the other four players are paired. (The player who sits out the round is the player who would normally be paired against the nonexistent sixth player in the six player round robin table.) Also, note that in a round robin, the player who sits out does not get a bye. The full point bye for not having an opponent only applies to Swiss tournaments. (There’s absolutely no reason to give every single player a free point for an unplayed game in a round robin.)
Tim Just has a good website to learn some ins and outs of being a TD. He also has lots of useful links there.
The 80/20 TD - here is a link
To avoid sitting out, you could have two double rounds instead of five single rounds. Each player plays two opponents at the same time.
For example:
1st double round: A-B and B-C and C-D and D-E and E-A.
2nd double round: A-C and C-E and E-B and B-D and D-A.
Arrange the tables (let’s say you are using tables that are 6 feet long and 30 inches wide) so that the short edges form a regular (equilateral and equiangular) pentagon in the center. The tables will spoke out like the blades on a 5-blade ceiling fan. The players play in the V-shaped areas formed by the fan blades. Each player plays white against the opponent to his left, and black against the opponent to his right. All clocks face the center pentagon so they can all be seen by all the players all the time.
Double the intended time control to compensate for the fact that each player is playing two games simultaneously. For example if you had intended G/30 with four single rounds, make it G/60 with two double rounds.
The biggest problem will be getting all the players to agree to this arrangement. You may have to sell it a bit. But once players realize they’re getting twice as much time, they won’t object so much to twice as many opponents at a time.
We did this often at the old Lunt Avenue club on weeknights when five players would show up for a one-evening event. The concept also works with three or seven players.
Bill Smythe
Creative, if slightly psychotic. 
Yes, very true it would be 5 rounds although this group consists of speedy and well as slower players, so my hope is that it will work out in that usually the player isn’t sitting out for too long. And yes, no bye.
Wow, very interesting. Maybe someday lol.
The idea of playing two rated games at the same time has always struck me as crazy. We used to have a guy in Nebraska who’d enter two sections of an event, once he entered THREE sections, and placed pretty high in 2 of them.
Until reading about this, I had no idea it was even legal to play multiple rated games at the same time. I must have skimmed that section of the book!
It is not stated in the rule book that it is allowed for one person to play simultaneous rated games. However, the rule book does not explicitly prohibit this.
I do not mean to speak for the ratings committee, but the rules committee asked the ratings committee for its opinion about this several years ago. The ratings committee has stated that playing multiple rated games simultaneously should not be allowed.
There are lots of things about being a TD that you never get from the book, just from experience.
Regardless of the Ratings Committee’s suggestion (they are not a rule-making body), the rules have never been changed to address whether someone can play multiple rated games at the same time. I’m not sure how we’d know it was happening during event validation, so it’d have to be on the honor system.
There are many rules that are, in essence, also on the honor system, because there’s no way to tell from a crosstable if they were followed or not. That’s one of the reasons why the chief or submitting TD has to indicate that the event was held in compliance with the rules.
I think a few simuls have been rated over the years.
What is usually going on is that a player is playing in 2 sections of a tournament. That is something I have done many years ago. Being eligible for a class section, and a higher section as well, means that there is opportunity to play in more than 1 section at once. The last time I did this I took a bye in Rd 2 of one section & Rd 3 in the other section. First round games are often lopsided affairs, so nothing major there. Last round is when you may have the big problem with trying to move from game to game.
I will admit that I did this in an effort to move my rating up quicker. The idea way back when was to play as many games as possible. I was young, foolish, and generally only used 30 minutes for any game I played then. So, playing in more that 1 section of a 40/2, SD/1 tournament was not that unreasonable.
I recall that the 1994 US Open in Chicago had 3 schedules of play. This included a daytime [10am] schedule and an evening [7pm] schedule. A player was allowed to play in multiple schedules, but at the merge of the schedules had to chose just 1 of the schedule scores to continue with onto the end of the event. Except for reentry a player should not be allowed to play in the same section twice. Can you see someone paying 2 entry fees with the idea of winning 2 prizes? That I believe is not allowed, or at least I know of no organizer that would allow it.
Larry S. Cohen
I think the reason for that was because playing two games at once impairs your effective skill level and thus impacts the validity of rating the games as if you had not been impaired. If both players are equally impaired (per Smythe’s suggestion) then the ratings committee might be more amenable.
When a psychosis gets to be sufficiently widespread, it becomes a great new idea. 
Not too crazy in this case, because both players are affected equally, and also because the time control is doubled over what was initially announced.
Bill Smythe
Under the Smyrhe method how do you do seating? Seems like the guys at the end would not have their second game side by side. I did the two section thing a lot when I was young and foolish, but my games were always next to each other.
Check his original post – the tables are arranged in a circle (or pentagon), so there is no “end”. Each of the five players has an opponent on each side.