These are what we call the 'YMMV items.' Things that some people find in this work. We call them 'your mileage might vary' because not everyone sees these things in the same way. This starts discussions in the trope lists, a thing we don't want. Please use the discussion page if you'd like to discuss any of these items.
Mission 15/18 in 2, "Which Way To The Coast?", you've given 40 years to complete your objective, and for a silver or gold victory have to do it in 30 and 20 years, respectively. What is that objective? Personal net worth of 10 million. And the map just happens to be wide-open and flat with plenty of industry and long-distance passenger routes waiting to be exploited. With any level of competency, which you surely have to get to this point in the campaign, you can get that net worth value in ten years.
Mission 17/18, "Dilemma Down Under" is similarly simple. For a gold, you need to have three consecutive years with excess of 1 million in profits. While the lack of passengers, your main income in most maps, is intimidating, the map is chock full of industries near your starting cities. With a bit of luck in the placements of those industries, you can reach the objective quite easily, as long as you're keen to squeeze every penny out of your trains.
Character Tiers: The managers of 2, though their groupings are not clear-cut, some are clearly useless and others will be employed for life once they apply. The former — any manager with only one effect, since inevitably another manager will offer that effect alongside others. The latter — William L. VanHorn, John Work Garret, Charles Melville Hayes, and Robert Gerwig for offering ridiculous discounts to construction, and George Westinghouse, George Pullman and Oscar C. Murray for significant boosts to train profits. Pullman for example gives a 25% boost to passenger revenue (read: the main source of your income in most any map), making him a near Game Breaker.
The AI opponents that focus on dominating you via the stock market. They can be nigh impossible to dislodge in Tycoon 2, to the point that if you see somebody like George Hudson or Jim Fisk in the game, it is usually a good idea to make use of your railway's early income (or even take on debt) just to buy back public stock until you control a bare majority stake in your own company. This then leaves you free to pump yourself up with dividends, buy up stock in their company, and hopefully put them out of commission.
It's still hard to actually eliminate an AI opponent; even if you take over their company, the payout from their stock can leave them with plenty of resources.
More track-system focused AI players can turn out to be this, if their rail empire grows to block yours in a significant way.
The last mission of Tycoon 2's vanilla campaign, for a gold, gives you 12 years to build a railroad crossing Africa and carry 4 loads of cargo between them. And it's quite difficult... if you start where the map spawns you, at Cape Town, at the foot of a mountain range with scarce resources nearby. However, you begin with access to Cairo, which has enough population to supply three trains running passengers to the southern cities, and can begin raking in large amounts of cash easily. And while the map is divided among territories you need to buy access too, you only need to access one of two to connect to Cape Town, and the German territory is dirt cheap. Coupled with a manager to reduce track laying costs and/or increase passenger profits, you can connect the two cities within just a couple years and send your trains down to Cape Town — it's a long trip, but it won't take them until the time limit is up.
The last mission in Tycoon 2'sSecond Century campaign is amazingly easy, particularly against the rest of the expansion which can be quite Nintendo Hard when it wants. The objectives are to get 15 million in book value, have the highest net worth of all four players (actual worth doesn't matter, just outrank them), and be the only railroad in operation. What makes it so simple is that you're given thirty years and some fairly flat terrain to work on, so making a profitable company is easy. With a bit of luck in the layout of resources you can easily buy out your competitors, the stock holdings needed to buy them out very likely giving you that superior net worth. With all three rival companies out of business you have the rest of the time limit to get your company to 15 million book value, and if you're profitable enough to buy out three rivals and add their track systems to your own, you're liable to have that by the time you're alone anyway, and if not will be able to get it easily.
Good Bad Bugs: In Tycoon 2, building track one tile at a time is cheaper than to lay out one continuous track. Sometimes this is because the terrain will be adjusted to make the track grade less steep, other times however, there seems to be no reason for it. Whatever the reason it happens, it can save a lot of money if you've got the patience to do it.
In Name Only: The Poptop sequels and Railroads didn't have any of the freedom, scope or open-endedness of the original game (and Deluxe). At least in Tycoon 2, however, a user can go into the single-player maps using the editor and remove the objectives, conditions and triggers that force a time limit on scenarios.
Most Annoying Sound: There is no option to simply restart a campaign mission in 2, you have to admit failure and select it again from the menu. And every time you resign, the narrator mocks you for it. "Couldn't quite pull it off huh? Weeeeeell that's alright, there's plenty of other career paths available!"
Scrappy Mechanic: In Tycoon 2, when a train travels between two different territories, it has to go through customs. What this means in terms of gameplay is that the train gets to the station and sits there for an additional month or so, the value of its cargo continuing to degrade. On the up-side, you can speed up the process, but you can't eliminate it.
That One Level: Any level that involves personal wealth. The only reliable way to make money for yourself is to run a successful company and get paid through dividends, buying back public stock when you can to increase your stock price. Unfortunately otherwise, the stock market of the games is very much like the real-life stock market, in that it can crash at any time. The more stock you buy the more reliant you become on its price staying high so your purchasing power doesn't go down below zero and you're not forced to sell back the stock to get your purchasing power back in the positive. The problem that comes up is that selling stock lowers the market price, in turn lowering your purchasing power again so you have to sell more stock. Repeat until you own no stock and are several million in debt. Oh yes, and rival owners can short sell stock, lowering it's price to start this descent into bankruptcy, and you can't stop them. This will happen. The only escape from the loop is to buy out other companies so your stock with them is liquidated into cash that won't fluctuate with the market, but that's only for other companies, takes a lot of money to do, and isn't so much an escape as a safety net that ensures you have at least some money when the market collapses and you lose your stock.
"Next Stop The 20th Century" in 2. Bronze objective — have 10 million in industry investments, easy, just buy lots of industry. Silver objective, also have an annual profit from industry of at least a million, and for a Gold, do both ten years ahead of time. The thing about industry profits is that they are ridiculously low, even if you have a dozen trains running industry cargo around supplying factories and such with what they need, you'll only be making a few hundred thousand a year off of them. This mission rounds it off by making you buy access rights to neighboring countries and giving you three AI companies to compete with. Oh yes, and each time you start the mission, the industries are randomly placed, so have fun restarting the mission over and over waiting for a winning map to appear.
Exactly the same mission got two game-breaking bonuses, that makes it one of the easiest in whole game. Building station in Luxembourg provides hefty bonus to trains speed (and can be achieved in no time), while conneting with a station anywhere in Russia provides a huge bonus to ALL revenue. All you have to do is going as far as Russia - and this mission in France-based. With those two, you can easily beat the mission a year or two after connecting with Russia.
Values Dissonance: The East Africa map ("Rhodes Unfinished" scenario). It's a fun map, and it feels awesome to be connecting all these African countries, but then you realize this is the late 19th century, and you are a European empire connecting African colonies. Puts an interesting twist on the usual ambiance of tycoon games.
There are also several maps set in the pre-Civil War American south which would mean that any agricultural enterprises the player purchases would likely be operated by slaves.