In D&D 5e, the daily rate of mounted overland travel is generally the same as on foot, because horses get tired and adventurers carry a lot of heavy equipment.
See the section Special Travel Pace in the DMG (p. 242–243). This section starts:
The rules on travel pace in the Player’s Handbook assume that a group of travelers adopts a pace that, over time, is unaffected by the individual members’ walking speeds. The difference between walking speeds can be significant during combat, but during an overland journey, the difference vanishes as travelers pause to catch their breath, the faster ones wait for the slower ones, and one traveler’s quickness is matched by another traveler’s endurance.
In the same section, the rule is:
- In 1 hour, you can move a number of miles equal to your speed divided by 10.
and then:
- For a fast pace, increase the rate of travel by one-third.
- For a slow pace, multiply the rate by two-thirds.
So an unencumbered horse with a speed of 60 could theoretically travel 6 miles in an hour at a normal pace. At a fast pace (a gallop), 8 miles per hour. That's "twice the usual distance for a fast pace", where "usual" means a creature with a speed of 30. This suggests that a riding horse with no rider, traveling alone, can cover 48 miles per day at a normal pace.
So the rule that "a mounted character can ride at a gallop for about an hour, covering twice the usual distance for a fast pace" seems to exist to allow for mounted travelers covering short distances quickly by using the mount's speed instead of "the usual pace", for up to an hour each day.
So, according to the rules, a traveler on a horse at a normal pace (3 miles per hour) will cover about 24 miles in an 8-hour day. If you make the horse gallop for an hour each day (fast pace for a horse being 8 miles per hour), that range increases to 29 miles. That's within the realm of what you would expect in real life, with a fast horse on good roads in fair weather.
Variant: Encumbrance
If you're using the encumbrance rule, a Riding Horse needs to be carrying less than 80 lbs of rider and equipment to get its full speed of 60. Loaded with between 80 and 160 lbs it has a speed of 50, and carrying between 160 and 480 lbs (its maximum carrying capacity) it has a speed of 30. A 200 lb adventurer in chainmail with a dungeoneering pack, longsword, and shield weighs in at about 325 lbs, so under this rule a horse's travel pace is usually the same as an unencumbered adventurer on foot.
As you said you're all right with consulting the lore of previous editions for an answer, I'd suggest taking a look at Planes of Law from Planescape, if you can get hold of it. (Not just for this particular question, but because it has an excellent presentation of Baator as a whole.) Fires of Dis would also be a great reference for Avernus and Dis in particular. The 3e Manual of the Planes also has a good overview of Baator that could help flesh out your planned adventure.
Anyway, on your particular question. According to a map provided in Planes of Law, as well as the individual descriptions in separate layers, there are the following inter-layer paths between layers (any without descriptions are referenced only on the map):
Further, there are direct portals from the Outlands to the city of Grenpoli in Maladomini, as well as from Sigil to both Grenpoli and Malagard. And of course, the main portal from Ribcage in the Outlands to Darkspine in Avernus. From Planes of Law: Baator, page 5, a general description of the state of portals out of Baator:
Most of the known gates [out of Baator] are two-way and are extraordinarily well guarded, preventing both entrance and egress. Anyone hoping to escape via these gates had better think twice, because the baatezu won't when they catch the poor sod. Most of these portals are build inside the fortresses of the major fiends of the layers. No one knows if the fortresses sprang up because of the portals, or if the portals just happened to appear in the fortresses after construction. 'Course, no one's really asking.
And from page 4, a description of the gate between Ribcage and Darkspine; this is from the perspective of entering Baator, but there's still some relevant portions:
The best route in is via a gate located in Ribcage, that "quaint little village" on the edge of the Outlands. The Cursed Gate, as it's called, is in a heavily fortified part of town; in fact, it's accessible only through the citadel of Lord Paracs, the ruler of Ribcage.
...
...the lord of Ribcage and the baatezu guards on this side of the gate have come to a tidy little agreement, one that profits both sides and doesn't bend the laws too far. Basically, the two parties bob travelers through the gate for whatever they can get...
Also, just as a note that's not especially relevant for you, earlier works suggested that the River Styx only connected to Avernus (as it connects to the first layer of all the Lower Planes) and Stygia. Of course, this isn't binding on later lore by any means, and that passage in the 5e DMG definitely does suggest otherwise as of 5e.
Best Answer
According to this source, the speed of a sailing boat depended on the waterline length.
The exact formula quoted there is
hull speed = 1.34 * sqrt(waterline length)
A boat with a waterline length of 50 feet would therefore go about 9.34 knots (~17.3 km/h or ~10.75 mph). This of course only applies on open sea with good wind.
I have not found any sources for the maximum speed on a river, but I guess it's safe to say that it would be half the speed, at best.
Those guys discussed something similar, and came up with an average travelling speed of 5 knots (~9.26 km/h or ~5.75 mph) for a trading ship with a waterline length of 75 feet. That would, of course, change depending on wind conditions, the river (Does it run straight or in a lot of turns?) and your direction on the river (Upriver, downriver). But I have no Idea how the exact modifiers are for this.
As for the rest of your questions, I have no idea and hope that someone else here can help you. Take this as a general direction, not a fully fleshed out answer. ;-)