Thanks for everyone who responded!

So yesterday we had a four-player game of 1889, and though I had a lot of fun and only narrowly lost I would say overall it went OK. I was hoping this could be the start of more 18xx games, but my general impression was it (or other 18xx games) probably won't be played again for sometime. This could be due to a few factors, one is I'm a horrible teacher of games and I often forget to mention rules until they become big-time game changers to me (or are perceived to be). Mea culpa. The game took about 5 hours which was a little longer than I had hoped for a 4-player game, but I think would be greatly sped up in future plays.

So this group had all played 1846, but as others pointed out that is generally such an oddball 18xx wise that a lot of rules had to be 'unlearned'. The biggest one it seemed is the whole 50% capitalization versus incremental capitalization. The end result of which was, everyone was incredibly broke the first stock round and only one company was 50% capitalized. We may have been playing it wrong perhaps? I think the idea is we should have been passing on privates more and generating income via the special privates-pay-out special rule. For instance I bid on the private that gives you a free stock cert for the yellow-line but I quickly realized that I had to use it immediately if I wanted to operate in the first OR, which granted gave me a cert at a small discount but deprived me of some much-needed early game income.

Another rule that caused some consternation was, what I believe they call on Heavy Cardboard as 'finger-waving', where you purchase a stock then sell it the next go-around to drop the stock value of another player. The first time this happened it was a genuine mistake as I purchased the wrong certificate and was at my limit, but it caused a bit of a fuss. Thankfully my stock was on a shelf otherwise I probably would have seen my stock punitively tanked in response. :D

I lost the game by about $300, though I had 60% of the most successful companies by stock value, I didn't have a diesel on my companies and wasn't making the $580 revenue the two companies with diesels were. I only had two 5 trains on one and a single 6 train on the other. I did had one token left that I could have used to block some of the lucrative routes but I wasn't able to transfer any cash to my company without severely hurting my income/stock-value for a round or two (I paid dividends every time save once). This was my biggest mistake and likely cost me the game, though I don't feel any negative feelings about it since it was our first game and I did come with the biggest advantage of being more familiar with 18xx games and the rules to this in particular.

The winner won by acquiring the first diesel, by first buying a 4-train from the other company then trading it in for a diesel. I thought this was a little odd to me, but I explicitly told him you could buy as many trains as you can afford. I had just never seen that before. I did make one player quite salty when I blocked his connection to my city by placing a town tile pointing away towards the mountains. I could be wrong, and I'm pretty sure it's the same as in 1846, but I believe he interpreted the rule that all track must respect previous track meant it must connect to adjacent tiles and not that it only applies to upgraded tiles. Also he purchased the Private that lets you place tiles on mountains for free but I don't think he used it even once and when he needed it, all privates were removed which I thought was funny (and I think fairly common?).

Well, thanks for reading this I really appreciate this community. Let me know if ya'll have any additional thoughts on how I could have played/taught this better. Also just wanted to mention, I really like 18xx games and I'd be happy to play online via tabletop simulator or Vassel if there is a regular group.