If gaara avoids using Wind release moves and avoids Jiraiya's genjutsu. I think he has a solid chance of winning. I'm not really sure, I'll wait a while and see what other people say before I make a definite conclusion.
like how danzo was too experienced for sasuke? gaara has been fighting in hellish conditions since he was like 4. both have particpated in war.the field looks in gaara's favour but jiraya is wayyy too experienced for a noob like gaara
he can make a swamp on a hard surface like a building or the ground. gaara doesnt fight on the groundhe can make swamp anywhere
oil by itself does nothing. its the special oily suiton of the mizukage that seeps through and breaks it downafter oiling the field the sand will be of little help
no it isnt. the onyl thing that can dmaage the sand is mizukage's oily suiton.jiraiya because of his collabs with ma and pa . gaara would take some damage knowing that jiraiya has OILLLLLL, which is one of his sands weaknesses
gaara has a perfect visual genjutsu defence. third eye. meaning he can close both his eyes but still see whats going on. sound genjutsu is countered by simply knowing it exists and then shoving something in your ears to block it out.gaara hasnt been shown showing defense against genjutsu so that could be another
he wont. the sand withstood steaming danger tyranny, madara's yagata tomoe attack, and deidara's C3. just punching it won't do shit.he would definly have the speed and strength to hit gaara whether it be his ninjutsu or taijutsu