TLDR Explanation of Regions, Stamps, and Servers Before update.
Right now matchmaking is a little weird for the Hourglass Fights. Its tedious, time consuming, and boring. Here is a little info that might help you understand everything I have figured out. Including why new players are getting hit with curse wielding sweats. We know matchmaking is bringing same-faction fights and that will be awesome. It will help with the fact that the Ghost Curse is desired way more than the Skeleton Curse. BUT we are ignoring that. What we are going to focus on is the organization.
There are REGIONS, these are real world locations like North America(NA) East, NA West, EU, OCE. Inside of the regions are STAMPS, a collection of single instances of the world these are called SERVERS. The issue lies in the fact that battles can take place with people on your SERVER and with people on your STAMP. STAMPS do not have a large number of SERVERS, im estimating as low as 4 or 5. For my example we will use 5 SERVERS per STAMP.
If there are 5 Servers, with a mix of boats. Lets say they are all the same 1 Galleon, 1 Brigantine, 3 Sloops. If you are a Galleon, there are 5 other boats of the same size on your STAMP. If you queue in and get stomped, and keep queueing, even if everyone is still there. Chances are you will see that same crew again very quickly. This is true for all boats, because even though sloop is a very popular boat, its split between duos/solos So its very easy to have a mostly dead stamp. This is why people run into the same opponents over and over again. This is why I recommend hopping servers if you get stomped, this way you might end up on a different stamp.
All servers within a stamp will have identical, sometimes different matchmaking times. When asking opponents what their hourglass said, it was almost always what mine was.
So now lets talk about why the Sweatiest of players are getting matched with everyone from experienced pvpers, to moderate players, to complete noobs.
The matchmaking is based off of a modified ELO system that takes into account the ratio of Wins vs Losses of the crew. So someone who is 200 wins 100 losses and wearing a curse has the same rating as someone who is 10 wins and 5 losses and just getting started. To add to this, when you dive it starts looking for opponents. But imagine matchmaking looking like an iris opening. As it opens wider and wider, more people are acceptable opponents. This means that is someone with a 100/0 w/l has been searching for a bit, their matchmaking could be so wide that when someone who is brand new or even has a negative w/l can be paired with them. This is because STAMP population is so low and matchmaking is based off of factions as well. It also applies the other direction. If someone is new and can not find a match and has been sitting there for a few minutes and a super sweaty crew jumps into the queue they may receive them as an opponent because their matchmaking has opened up wide.
If you sit in matchmaking for more than 10-15 minutes. It means one of two things there is no one on your stamp fighting or the only other two people fighting in your ship configuration are actively fighting. If the other person on your faction wins and their opponent quits. You have a dead stamp and no one else to fight. These issues can be resolved by hopping servers by starting over. Also if you keep queuing into the same people and getting stomped, try a new server.
I hope this helps. Any questions let me know. I'm just trying to help people understand and alleviate frustrations while we wait for an update. This information was gathered by me and my friends in our grinds past 200. We know we are on the higher end of the food chain, but we want everyone to play this mode and are very (im)patiently waiting for the update ourselves. And again to close, I hope they add some sort of daily incentive, some sort of "gold rush" to allegiance battles, and more rewards before level 100 and after 200.