My campaign just entered the Anarchy era. We played through the battle of st Albans and Uther died soon after. During this one of my PKs died, and he was the last legitmate heir.

He has an older illegitmate brother, the second son - the first also having been illegitmate (and now deceased). The player started playing the third son (the first legitmate son), and then when he died, with no male heirs, he played the forth. Now that son is dead only the female offspring remain, who are no more than 4 or 5 years old.

Desperate to continue with some connection to his family and old lands, the player concerned has been suggesting various workarounds, all related to the second illegitmate, unkighted son. Now I want him to have some chance but I don't want him to have it too easy. The other players have had to walk the tightrope of getting a legit heir so I don't want to set too many precedents making illegitmates just as worthy.

So, some questions;
The legit PKs young daughter is now the only rightful heir. If the illegitmate were to kill her off would that make life a bit easier for him (assuming he wasnt found out) as he would then be the *only* living family member?
This is the Anarchy phase. Could he just seize the land and defy others to come take it from him?
Could he attain knighthood by swearing loyalty to the Countess? He's 35 so too old to become a squire,. Would his illegitmacy cause problems here, eg would it ruffle feathers with the other knights of the land.
Could he marry the widow of the deceased PK and assume some control of the manor? I would assume this would require the say so of the Countess.

Any suggestions welcomed.

The legitimate heir is the deceased PK's daughter. The biggest problem for the illegitimate bigger brother of the PK isn't so much the daughter but his own unknightly status, in my opinion. If he were a knight, then he would have a much better chance of either pressing his claim, or at least get appointed to oversee the manor until the legitimate heir is old enough. Naturally, if the legitimate heir (the daughter) is dead (and nothing to point to the bastard uncle), then things might be easier, as the manor is up for grabs. However, if he is an unknighted 'civilian', his chances are very poor even then, as the Countess would be better served to just ignore the bastard totally and use the manor that has defaulted back to her to bribe some famous knight for his loyalty and support.

Of course, if he is a famous warrior albeit unknighted, well then, he is in a much better bargaining position. The Countess needs good warriors/knights even if she dislikes trampling over a child's inheritance rights (bit too close to comfort, given Robert's situation), and probably wouldn't mind elevating him to knighthood, too. His illegitimate status makes things a bit shakier, of course, but this is Anarchy we are talking about here. His legitimate cousins, if any, might make some noise, though.

Alternative suggestion: Does the mother of the daughter (i.e. the widow of PK) have any knighted brothers? Perhaps one of those might be appointed as guardian.

I think medieval church had things to say about marrying your brother's widow; that it was basically incest. Which is why Henry VIII needed a papal dispensation and a testimony from Catherine of Aragon that the marriage with Henry VIII's brother Arthur was not consumated. However, you can play fast and loose with that one, if you wish, and allow cousins/brothers to marry the widows, to keep everything 'in the family' as it were.

In our campaign, the usual option is to bring in a newly knighted cousin to oversee the manor, with the expectation that the normal PK Glory-gathering spree will eventually lead to a manor of his own, probably around the time the legitimate heir is old enough to be played. Actually, we do have a similar case in our campaign right now... The PK died and the legitimate heir was a young child of the feminine persuasion. So the player switched to playing a cousin with a son, with the understanding with the GM that once the son becomes a knight, he will get to marry his second cousin, the heiress.

The cousin option sounds good.

However if the player has his heart set on playing the bastard why not flip it.

The cousin usurps the lands and basically imprisons the young daughter, planning to wed her and secure his claim in time.

Though the countess does not like it he still meets the terms of the grant in knight's service and has enough allies at court to mean she turns a blind eye for expediency.

This is a chance for the second son, long-forgotten, to show his quality. Maybe he goes to the other PKs, asking to be taught how to fight so he might prove to the world he is no baseborn villain.

If he defeats the cousin and upholds his sisters claim he is knighted and administers the lands until her marriage.

Good suggestions. I put the cousin idea to the player and he liked it. However, his interest has since cooled. He's now looking at creating a totally new PK & Family etc,. I think his character's death prompted a moment of panic and desperation that has now passed. But I'll keep the idea in mind the next time a similar situation arises. Don't you just love the generational aspects of Pendragon!