No. God was not necessarily being "extra nice" to Gideon by honoring his request for two signs. Though obviously a bit insecure, Gideon was not "pressing his luck" when he asked God for two signs. He did not quarrel with God, nor did he question the presence of God by requesting the two signs.
The Israelites, as recorded in Exodus 17, did, however, quarrel with Moses (and hence with God) and asked out loud, "Is the LORD with us or not?" There is a big difference between the two incidents.
For one thing, Gideon was not the most confident person the LORD could have chosen. Nevertheless, when the angel of the LORD first appeared to Gideon he said,
“The Lord is with you, mighty warrior” (Judges 6:12, excerpt).
The significance of that utterance was a reminder to Gideon (and to us today!) that with the LORD on his side, he had nothing to fear. Not only would God be his strength, but Gideon could be assured of victory in what the LORD chose him to accomplish.
For a second thing, Gideon was not putting God to the test, as were the Israelites at Massah and Meribah. Gideon's requests reflected neither his distrust of God nor his doubt that God had appeared to him. Lacking confidence, he just needed a little confirmation and reassurance.
For a third thing, Gideon's attitude reflected his reverence for God, and when God consumed in spectacular fashion, with fire, the food Gideon had specially prepared for him, Gideon realized he was indeed in the presence of the angel of God.
Is "putting out a fleece" today an indication of having a quarrel with God or of entertaining doubts about God's very existence? No. I would, however, caution against using the "fleece method" regularly or habitually. After all, Christians, as with God's saints throughout history, are to walk by faith, not by sight (see, for example, 2 Corinthians 5:7 NIV).
Years ago in Bible college, I had a teacher who earlier in his life had applied to the Wycliffe Bible Translators to become a missionary to a people group not having a Bible in their heart language.
Obviously, this step was a big one for my teacher, but he was convinced it was the right thing to do. When the commitment papers arrived in the mail, he was ready and eager to sign them, but for some strange reason he could not remember his name! To him, that was a sign from the Lord that becoming a Bible translator was not God's will for him at the time.
From that time in my teacher's life to the time he was my teacher, nothing similar had happened to him. He told my class that his forgetting his name was likely going to be the only sign God would give him in his lifetime. His testimony was therefore a cautionary tale, as it were, about limiting one's requests for assurance from God.
Again, God's children are to walk by faith and not by sight.