My apologies if my response is a mess but I tried to give you as much info as possible. See below.
- Is leaving at the pool entrance the only place to start?
Technically no, but if you want to do the routes the "normal" way, yes. For Overlode, I would not try going backwards (although I've been tempted to see what it's like), it would be dangerous going up some of the normal-way descents if you run into someone going the other way.
Here are the possible routes, although you may be able to figure out some others.
The pool parking lot. If you start at the main trailhead entrance (by the bike wash) this starts the mound loop (west side of park) and also leads to Overlode and Pokerville if you take a right at the first gravel crossing, and cross the road. The ski trail forks then immediately... if you go left you go downhill to Overlode (although technically you can follow it around and still get to Pokerville, since it's a loop). If you go right, go downhill and take another right at the next fork, and cross the road, then quickly after that Pokerville starts on the right.
Taking Overlode will lead you back to the mound loop, but I often bail on Ryan road like you did if I'm tired or short on time. You can then technically ride the trail backwards to the trailhead (pool lot).
Taking Pokerville will lead you to the SW side of the park, and since it's an out and back currently, you either ride it all the way back, or you can just backtrack to the blacktop crossing if you go up the hill, takes you into the campground. There are two gravel paths that lead north from the campground. The closest one is a longer climb but you get to descent most of Home Stretch, backwards towards Holy Schist. The farther west gravel path is shorter (you have to go through more of the campground, though) and this takes you right to the end of Holy Schist. So basically if you ride Pokerville you can also ride Home Stretch and/or Holy Schist backwards.
Now, if instead of Overlode or Pokerville you continue around the mound, there is a bailout on Serpentine Climb before Holy Schist (you'll see a tight right switchback turn). This bailout goes back to the pool parking lot. You can also ride this backwards if you want to skip right to Holy Schist the normal way.
Basically, there is a short mound loop (bailout before Holy Schist), a long mound loop (includes Holy Schist and Home Stretch). You can then also add in Overlode to the beginning of either of those, which will tack on about another hour or so.
- Can I do Pleasure Valley and get back? Or how strict are the one ways? (sorry probably a dumb question) It seems like if you start at the pool lot and go East there is really only one way to get back in (from the North). Is this accurate? This one is kind of big because I'm a beginner. I went out on Over Lode today and it pretty much demolished me. I ended up ditching off on Ryan and riding back into the park.
I think I answered this above, the only one-way that I would consider strict is Overlode (which is the singletrack in Pleasure Valley). I also generally never do Serpentine Climb back to the pool parking lot as it's hellish that way, if I ride Holy Schist backwards I just take the bail out.
- Where to start on Pokerville?
I covered this above.
- Maybe it's because I've been out twice, but the climbs on Over Lode were really tough. I had to walk most of them eventually. Any suggestions for smaller hills I can use as training?
Yeah there are a couple tough climbs out there, walking up is good training too, but the rest of the trail system has no climbs like those, with the exception of the monster on Holy Schist.
- Does anyone have graphics of elevation for any trails from GPS tracking? I will get them from my phone soon enough, but it will take me some time to get to all of the trails. (Probably until next summer before I can ride Holy Schist!) PLease post them here if you have them, otherwise I will as I get them.
Walter Hougas might have this, but I've never seen a topo map with the trails overlayed, that would be sweet.
- What would be REALLY nice if someone had the time would be to make copies of the map and highlight in red all the possible loops, I wish I was knowledgeable enough to do this, but perhaps someone could do it rather quickly who has the knowledge?
This has been done to some degree via recent signage. If you look at the arrows on some of the sign posts, there are color coded arrows. I think there are four colors representing the four possible loops that I mentioned earlier. The colors I think also correspond to the colors of the trails on the signs themselves, but I'm not 100%.
- How late into the fall are the trails open?
Good question, I'm not really sure now. They used to close them in the winter, but now they may leave them open. There's snowshoers though and I'm not sure if they take priority or not. We try to get out and blow leaves as soon as feasible and some of the best riding (IMHO) is right after that is done.
- Where can I check to see if the trails are open before driving out there?
Call the park office: 608-437-5711. If they don't answer, you can post here and ask, or click on the Trail Conditions link and look at the most recent posts. There's also a large sign at the park entrance/office. Also, use good judgement, avoid riding if the trail is packing into your tires.
Good luck and have fun!