He saw how Judith seemed delighted when he mentioned that one idea that he always kept in his mind, with a laugh she mentioned how her husband and daughter are or were sword fighters. So she expressed an interest
"Ah, I see... well, I would love to have you if you happen to be in an area" certainly gave him motivation to do it "Ah and sorry about your daughter" it was only fair and polite to say it. One cannot simply ignore the dead daughter sentence. Just a small courtesy. He did see the way she talked that it was already a distant past and what has happened has happened and was met with acceptance. Wounds that healed.
He looked at her as she spoke up once again, and this was a curious thing. Well actually not really, it was a great thing. It was funny she was giving him time to reply, but he didnt need to think it over
"Lady Judith, it would be an honour to be allied with you." he spoke with his hand on his chest and a minor bow; and he continued "Feel free to speak to Lady Alisa. I do not mind waiting as I am not opposed to such an idea. If we were to ally with Fairy Tail, I do feel the citizens of Baska would feel more at ease with my people."
Having a prestigious guild such as Fairy Tail be allied with you is like getting a grand seal of approval. People wont be as fearful around them, but more welcoming. Plus he would make sure to be good PR for his guild and show people that they arent all that bad. He can show people about swords and ease them in this kind of lifestyle, who knows maybe one day he inspires someone to join