For flights monitor SkyScanner daily, I've found the best prices for my trips came;
12 months from travel (LA, 2014)
8 months (New York, 2015)
3 months from travel (Seattle, 2015)
4 months (Boston and Washington, 2016)
5 months from travel (LA, 2016)
Airlines do have sales and offer deals so watch out for those as well. Generally speaking until 3-4 months before departure the airline doesn't need to actively push sales so the prices will normally be slightly higher. When it comes round to 90-120 days before the flight they evaluate the spare capacity and then price depending on how many seats are left (high prices for hardly any seats, low prices and sale deals for lots of seats). It really is impossible to work out, by monitoring SkyScanner over a few months you can see what a 'good price' is and then when that comes available snap it up.
Virgin Holidays were cheapest for me with car hire recently, but I'd still check the usual places (CarHire3000, USCarHire etc...).
Thanks.
Looking at around £520 to Orlando with Norwegian. Is it likely to get any cheaper than that, bearing in mind the whole devaluation of the sterling thing?