I barely got started with testing how much they ask for, but I am guessing that they ask for more. Based on some of the testing I have done, I'm guessing that if their sailing level plus their battle level totals certain amounts they will ask for more...so you would have a few levels to play with.
Miguel will always be found in the inn/lodge, unless he is part of a "job" you are working on...for example a collect debt mission or a find item mission. You still won't be able to treat him to increase his loyalty, just that you will probably have to ask the waiter at the pub/cafe to get him to appear.
Anyway, it is possible to get Miguel to 30 loyalty if you can get him to ask for a raise before leaving port, hire him a second time and get him to ask for a raise again and hire him for a third time. Of course you do have to refuse the raises, but once he gets past 30 he won't ask and you can't get the ten bonus for hiring him.
Sorry, rambling again, in short yes it is possible if you raise their levels you will have to pay them more when you hire them to begin with.
Another possible solution, save your game and give your mate a raise of 100. Then try to give him another raise, if he refuses and says he is happy working for you, reload your game and try 90 to see if you get the same response. If you don't get that response on the first attempt, reload and try 10 or 20 more to see if you will then get the refusal. If they refuse a raise they are at 100 loyalty. (wish I had thought about that earlier) 😀
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