Had another go at this, just for variety.
This play was started by using
RoR's trick of opening the game, opening the map, immediately returning to the main menu, then opening the map again (ie: to get a good random distribution of resources). The resulting seeding is interesting. It has a good range of resources spread across the map, but
almost no cargo at all west of El Paso. This means that the track from LA to El Paso will initially have to be laid as burn track, because there is no realistic chance of it being at all profitable. It also means that once El Paso is connected to the eastern network, profits in the western region should be astronomical.
Anyway, I did something different this time with the robber baron tricks.
Taking out a bond with SP is good for personal cash (because SP can buy back more stock) but it's a nuisance if you want to merge SP early in the game, to stop the AI doing stupid things with SP. If you don't take out a bond in SP you can merge it anytime for a few $k, without incurring any debt load. So, this time I accepted the lower personal cash from asset-stripping SP sans bond. I also didn't bother trying to get rid of every last dollar in SP. I just bulldozed the station and left the track segments alone. SP ended up with $22k left over and 5 track segments. This meant that, instead of the $943k that is possible with a bond, I ended up with $695k. After checking a few trial buy-ins, it was clear that $695k is only enough to get a controlling interest in the New Orleans company (GH&SA). That was the only viable target for the next step.
I decided to wipe out GH&SA completely. It's not necessary to save a track starting point in New Orleans, because any company you decide to keep can easily build to New Orleans later. So I took out a bond, bulldozed everything, and bought back as much stock as possible. There was $111k of company cash remaining, but I left that. It turned out that stock price still dropped to $1 anyway (ie: maximum profit for me) and that $111k will be handy for the next stage. So, after the usual resign/dump/clear shorts I now had $1,053k personal cash. That was enough for a controlling interest in the Wichita company (CRI&P).
So, buy into CRI&P, and take out a bond as the first step.
After that cash is secured: immediately buy up all available GH&SA stock, and then merge GH&SA at the minimum slider setting (because I won't need a few extra $k myself). This is where the remaining $111k in GH&SA comes in handy. It means more cash available for bulldozing and buybacks in CRI&P. So, do the usual tricks to CRI&P. It is left with no track or buildings, $1,000k of debt, and $22k of company cash. I now have $1,298k of personal cash. That's enough to get me control of the Santa Fe company (AT&SF).
AT&SF was treated the same way I handled CRI&P. Take out a bond first,
then merge CRI&P into AT&SF, then asset strip AT&SF. This boosted my personal cash to $2,108k which is easily enough to get control of the last company: Denver & Rio Grande Western. D&GRW gets the same treatment as before, with one minor exception. I deliberately left the medium station in Durango. My reasoning was that this should tie the defunct company to that location, so it would be prevented from doing stupid things where I didn't want it. So far this seems to be working.
Whether it will continue to work is another matter. We shall see. Never underestimate the inventiveness of RT3's Artificial Stupidity.
I then bought up all available stock in D&GRW. Why? Because it only cost me a few $k, and it means I can always take control of D&GRW if it decided to do something inconvenient. Personal cash was now $3,010k. That's easily enough to take over Texas and Pacific, which becomes my main company. As soon as I take over T&P I merge SP into it, for the princely sum of $42k. I now have my starting point in LA for a bit later. Then I issued two lots of stock and took out a bond, which gave me enough cash to upgrade the 3 medium T&P stations to large stations. After checking the cargo map I knew the larger stations would pay off immediately, so it was worth doing. You have to bulldoze a couple of houses to upgrade the Waco station, but I still had enough cash to buy a couple of trains. The first year generated $1,228k of profit from rail alone.
So far I have played until January 1866. I built a lumber mill in 1863, and bought two associated logging camps at the same time. The economy dropped into recession for 1863-64 and returned to normal during 1865. Profits for those years were $731k/$786k/$1,556k. It's definitely looking winnable from here.
This progression of asset-stripping companies is definitely the best way to clear territory and maximise your personal cash. It also means your company is guaranteed to have the highest CBV. On the other hand, I don't yet know if it will be the most profitable for fast expansion. It's possible that taking out a bond in SP (and accepting the merger debt load there) and only trashing CRI&P/AT&SF/D&GRW, and then playing both the New Orleans and Fort Worth companies, could be better overall. That is also arguably a more interesting way to play, because there are more factors to juggle (at least until you merge SP/GH&SA/T&P).
One thing I did do after taking over T&P is to smooth its track. All the track on this map looks like it was laid by AI, or by a human as careless as the AI. With a bit of terrain tweaking in the editor (with the game paused) it's possible to get T&P's track looking very nice. Even the bridges can be made presentable without much effort. It's probably worth having an already-smoothed version of the map stashed somewhere.