Complex trip planning guidance

I've done a couple Amtrak trips, but now I want to do a "bucket list" trip, Dallas (home), Chicago, Portland, LA. Dallas with a couple of days at each city. I'll be staying with family/friends so I don't need hotels or rental cars. But I do need some help. The Amtrak site is pretty bad for planning, their recommendation is just to keep trying multiple itineraries on different days. Getting a roomette/sleeper seems to rule out Railpass or any discount programs. Most of the non-Amtrak web sites are geared towards the first time traveler or those wanting vacation packages. Am I stuck with brute force and ignorance or can anyone recommend the best way to approach this?

You CAN Upgrade to a Sleeper when you use a RailPass as your Rail Fare!( you buy the Rail Pass and make your Sleeper Reservations in advance at the same time if this is Cheaper than paying the current Rail Fare in Coach for each leg of your trip).

Use amsnag.net ( developed by AU Member Paul M.) to check out Rail Fares and Upgrade Prices to Sleepers for up to 30 Days at a time and up to 11 Months in Advance.

This way you can compare what a RailPass would cost you per Leg of your trip compared to paying the available Low Coach Rail Fare for that Leg when you book a Sleeper

If you are flexible in the days you travel, you often can save Hundreds of Dollars using amsnag.net!

Hope this is clear???

Hopefully you're aware the train from LA to Dallas only runs 3 days a week - SuWeFr - between LA and San Antonio.

Since the SL run just three days the sleepers sell out quickly and are pricey because of the demand. The sleeper is switched from the TE/SL at night. I watch the fares since they go up and down based on how much is sold and how many days/months away from departure. Continuation can save too. We were going to stop in LA from Austin, but found we saved a bundle skipping it and going straight to Seattle, then skipping Chicago for WAS, but got a deal and hit Chicago on the return. Use the site above but come back regularly to check the fares. If nothing sells for 30 days the fares may drop, but if several people purchase then fares go up. Its just like the airlines, rental cars, and hotels. Early doesn't always get the lower fare.

You consider a travel agent. Mine specializes in Amtrak trips

Previously, I used some Travel Agents, but when they started to charge a fee, I found I could do my own reservations better than they did.