Thanks for the replies to my questions, I'll be sure to look over some of the older stuff in the handbook. Anyways I think I'll weigh in on what I've been doing so far in terms to the siege battle (As surprisingly the party has spent 2 sessions doing the meeting of the lords) and managed to 'kill' my version of Miha the Spy which was an exciting battle, who knew a Gate to Avernus with round based spawn could terrify my players so bad. It was great fun and the players had to use the staff of life after someone got killed by a beefed up Sivak Draconian who had some class levels.

Anyways, I've used a variant map for Brindol as I didn't like the layout of the Vanilla brindol and didn't have the time nor will to remake the entire city. Would have been quite painful, but I regret not taking the time to do so as I've noticed a few issues. Currently, this is what the 'Battle Map' of Brindol looks like, it may change as they are super paranoid about the Spy being alive.

Spoiler: Brindol Map
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Each of those squares is the various 'units' which Brindol has at its disposal, after changing many a number, it clocks in at around 10,385 troops for Brindol (Including all the Mercenaries they brought in and the many peasants 'conscripted' into the army. Each unit has a few primary stats, those being Soldiers/Size of the unit, Attack, Damage, Defense, Armor, Health, Speed and Moral with some lesser stats thrown in there to help out. I will admit, I shamelessly acquired the template from the Total War formula and made it all d100 based for quick action using the states as a framework.

Heres an example of some of the units

Spoiler: Units
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I've also made many new 'missions' and 'encounters' for the players to take part in, with a good chunk of combat going on overall the walls at first, akin to a proper siege. Where the Redhand tries multiple attacks to take the walls or breach them long before the 'Assault' in which the Redhandwill break through and storm the city. Thankfully not nearly close to there full number as the Brindol defenders would be crushed in a full out attack, considering 70% of the defenders are barely trained and could hardly be called an Army. The walls will be there saving grace.

My players noted this actually and during there first discussion with the lords before they went to meet the Ghost Lord and try to sway the guy to help him (No cleric or Paladin in the party, and the players figured this guy was being blackmailed), they advised the Council to tear down the orchards and nearby woodlands along with harvesting everything so the Redhand would A. Not have any cover B. Be forced to collect supplies elsewhere and C. Find wood elsewhere. Meanwhile, the defenders can use that sweet sweet wood to create Hoardings and Pallaisdes.

Which brings up an important aspect I feel in this module which is overlooked. The Environment favours the Redhand unless something is done. If those Orchards on the Western side of Brindol have left their hats free cover and concealment right up to the walls. And if the defenders fail to see anything, then you have can have a small yet sizable assault going on without anyone knowing.

Anyways, my players having arrived at Brindol about six weeks ahead of the Redhand had plenty of time to go ahead to talk to the lords and go deal with the Ghost Lord, they convinced the Council to use the wood for Hoardings across the walls, which offers more cover to archers and make Siege Towers/Ladders less effective. Something which may be enough to even out the 3:1 ratio and Veteran army that the Redhand has. They also had the mages and common folk (a few thousand peasants live in brindol so it's easily accomplished with magic help) to dig a moat, then the stone wall the sides of it. Moat is about 15 wide and 10 feet deep. That along makes attacking Brindol all the harder.

Now the Redhand has to either fill the damn thing which is time-consuming unless you have magic, which means putting your casters at Risk of the Defenders Casters and Arrow spam. Making it now a costly affair. Or the Redhand can simply do it the old fashion way and use dirt. Or one of the more fun ways! Siege engines! Something the Module doesn't even mention for some reason, where is the Siege Towers? But that's another problem. Anyways, some quite advanced designs that the Redhand could feasibly use if given the time.

Spoiler: Advance Moat Crossing Siege Engines
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Seeing that the Redhand has shown the ability to swiftly produce working Siege engines at the beginning of the module, it's not hard to assume they could create some manner of contraption that lets them cross their troops into a breach of the moat. Or even make rafts on the other side of the river and cross like they did at Drellins ferry. Something that would force defenders to deal with, as you at best will have some palisade walls.

The lack of siege warfare I think is a little saddening which is why I added a few days of besiegement as the Redhand does have a time limit, but they can't just rush the walls without a losing a significant portion of there troops. It makes more sense to widdle down the defenders and make some soft points or even breaches before assaulting the city with everything they got.

Overall, I feel that the Siege of Brindol in the Module is more of a mad dash rather than a proper siege.