I recommend getting the highest tonnage MASTERS license you can, to a point.
https://www.dco.uscg.mil/national_maritime_center/
Your experience will determine what you qualify for. Once you go over 200 tons, there are training requirements that change the math a bit. Do you want to pay for fire fighting training every 5 years at renewal time?
A masters license between 25 and 200 tons is easy to manage and renew. Unless you are working on the water for a career, I don’t know that a greater tonnage license is useful. I will be working on my 4th renewal in a few months.
If you don’t have the sea time for a masters, you can apply for an Operator of Uninspected Passenger Vessels or OUPV (also called charter boat license and six pack). You can upgrade to a masters later. Don’t inflate your numbers to get where you want to be now.
All the checklists and FAQ are at National Maritime Center website (link above). I recommend getting familiar with the requirements of each respective license, as well as the terminology, to inform your decisions.
If you use an APPROVED school, they can streamline the process. The ones I am aware of can administer the examinations on-site. I can recommend Maritime Professional Training in Fort Lauderdale.