It is always a bit difficult to balance a map, especially for those who want it "dead easy" at Investor level and "tough" at Robber Baron level. Uganda is mostly aimed at the experienced Robber Baron like yourself, who has seen it all, but it is quite doable (even starting from Kigoma) without a brute force approach, if one uses the loop technique explained above.
As shown in the map below, one needs five loops to complete the goals.
The challenge in Era 2 is that everything needs to be done amost simultaneously: First start growing Tanga and environment to accept goods, then link Dodoma and Mwanza to start mail transports, and then deliver emergency wood supplies as soon as Tanga accepts Manufactured Goods. AND start those passenger deliveries to Tanga, Dodoma and Kigoma!
Two useful tricks are: start the Tanga link in the last years of Era One, don't wait for the goals to complete. Money is not scarce anymore, so start connecting Tanga, Dodoma, Mwanza as soon as possible. Secondly, the net worth goal can be achieved easily by buying up your shares at the end of Era Two. As soon as you have hit the Net Worth goal, you are free to sell shares again, to finance that looong loop to the oil fields north of Kampala.
Loop construction is quite easy, but needs a bit of concentration when planning. What one does is to leave a gap in the parallel track when crossing the resource "green connection area". The gap is then filled with a single track connection. Now when building, say, a grain farm, the annex will connect only to one of the rails. This way, the trains can be forced "left" to farm A when leaving Dar es Salaam, and "left" again to farm B when leaving Tanga. You can check that the single connection has worked as intended by clicking the annex building (green arrow). Only one track should light up (white arrow). Note how the grain trains (including two passenger cars) are dutifully keeping to the "right" rail in the screenshot. This is a good way to fix the lack of routing control (no depots as in RRT3) mentioned in a previous post.
