Should I indulge a bit before going cold turkey?
No! This will make it so much more harder. It's like jumping into a freezing lake. You need to ease into the practice. Prepare while you can! The practice is very gradual and cannot be perfected without effort. That being said, the retreat may give you lots of experience but there's no guarantee you're going to come out enlightened.
Should I start practicing silence and eating less meat beforehand?
Practicing silence may help you out, but I'm not sure about eating less meat. That's not really essential.
Do you have any advice for me to help increase my chances of success and hopefully making it through the program and birthing a sitting habit?
Relax and take it slow. Don't get obsessed with being a "mindful person", just do the practice — put forth right effort. Neither "Right Effort" or "Right intention" are synonyms for bhavatanha (desire for becoming). Right effort is just putting forth the actual effort and persistence to abandon unskillful qualities and cultivate skillful qualities, right intention refers to skillful intentions — abandon intentions of ill-will, harmfulness, and sensual desire; cultivate good-will, compassion, and renunciation.
Just do the best you can!
Some wise words from Ajahn Chah about going on retreat and coming back:
If you are maintaining sati as an even and unbroken flow, it's as if the drops of water have joined to form a smooth and continuous flow of running water. Sati is present in the mind from moment to moment and accordingly there will be awareness of mind-objects at all times. If the mind is restrained and composed with uninterrupted sati, you will know mind-objects each time that wholesome and unwholesome mental states arise. You will know the mind that is calm and the mind that is confused and agitated. Wherever you go you will be practising like this. If you train the mind in this way, it means your meditation will mature quickly and successfully.
Please don't misunderstand. These days it's common for people to go on vipassanā courses for three or seven days, where they don't have to speak or do anything but meditate. Maybe you have gone on a silent meditation retreat for a week or two, afterwards returning to your normal daily life. You might have left thinking that you've 'done vipassanā' and, because you feel that you know what it's all about, then carry on going to parties, discos and indulging in different forms of sensual delight. When you do it like this, what happens? There won't be any of the fruits of vipassanā left by the end of it. If you go and do all sorts of unskilful things, which disturb and upset the mind, wasting everything, then next year go back again and do another retreat for seven days or a few weeks, then come out and carry on with the parties, discos and drinking, that isn't true practice. It isn't patipadā or the path to progress.
You need to make an effort to renounce. You must contemplate until you see the harmful effects which come from such behaviour. See the harm in drinking and going out on the town. Reflect and see the harm inherent in all the different kinds of unskilful behaviour which you indulge in, until it becomes fully apparent. This would provide the impetus for you to take a step back and change your ways. Then you would find some real peace. To experience peace of mind you have to clearly see the disadvantages and danger in such forms of behaviour. This is practising in the correct way. If you do a silent retreat for seven days, where you don't have to speak to or get involved with anybody, and then go chatting, gossiping and overindulging for another seven months, how will you gain any real or lasting benefit from those seven days of practise?