If you enter and leave in under 60 days you will not require any extensions under tourist exemption
If you re-enter after a period of more than one day you will be eligible for another 60 day stay under tourist exemption and can apply for a 30 day exemption
You could technically leave every 60 days and comeback after a few days but they will likely question how you can afford to be on holidays for this much time and suspect you may actually be working... financial proof will likely get you a pass
If you are staying over the 60 and 90 days, you should try to get a multiple entry visa - ie the visa that most fits your stay period