I was just in Florida last week for a week and did 2 hair/makeup trials! (We live in New York and are planning to get married in Miami, FL). The first trial went ok, the second one went awesome!
So here's the bad news.. After a few days, my planner contacted the second stylist to move forward with a contract. She found out that the stylist has a serious illness and is going to focus on her treatment and recovery right now. 
She said that if she gets better by next March, she would love to do my hair and makeup but she just doesn't want to commit right now, which is totally understandable.
Good news: My planner did tell me that the stylist's business partner also does an awesome job and she is available on my wedding day too. They work together all the time at weddings and the lady who did my trial usually does the hair and her business partner usually does the makeup. My planner said they both have very similar styles and always do a great job. The stylist's business partner would get details on how the stylist did my hair, and would be able replicate it for me on the wedding day.
So since I won't be going down to Florida until later this year (probably around the holidays in Nov/Dec), I'm wondering if I should just book with the second stylist's business partner since they both have similar styles? My concern is that I haven't done a trial with her though and I wouldn't get to until Nov/Dec. There's also a chance that the second stylist gets better and would be there on my wedding day to do my makeup/hair.
Do you think it is too early to book a hair/makeup stylist? Would waiting until Nov/Dec be too late?