For a money management app, I use Money by Jumsoft, though I will say that it's not perfect, just one I can work with. Syncs Mac <-> iPhone, which is very handy. http://www.jumsoft.com/money/
Everyone's different, but my strategy with the cash would be to keep an emergency fund in a high(ish) account, say £10k. I have no desire to deal with the hassles of landlording, so the rest I would move into Vanguard Lifestrategy 100 (it's an index tracker fund). £20k of that would be in an ISA (that's the maximum for the 2017/18 tax year) and the rest in a regular share dealing account. Then each year on 6th April, move the maximum allowed into the ISA, until it all becomes tax sheltered. But other people do like property, and make it work for them.
With a paid-off house you could comfortably save a grand a month, not per year as you are now. The standard advice is to understand track and understand your spending (which you want to do). After that I would look to combine two aims: improving your quality of life while reducing your outgoings. I switched from driving to cycling for my commute, and as a result I'm fitter, happier, more productive – and I'm saving £60 a month in petrol. I don't buy clothes very often (any more), and I plan carefully, buy quality, and end up with a more minimalist wardrobe (and minimalist look!) that makes it much easier in the morning.
So yes, track your outgoings. If you are spending £600 a month on going out, or clothes, or knick-knacks, then you can look at the happiness that brings, and contrast it with the happiness you will enjoy when you're not beholden to an employer.
on OSX and iOS I use the Money app. I just added a cash account and set it up as a new currency, then input the exchange rate, and it lists my BTC finances against my GBP. Works pretty well. Only thing is I have to manually input my bitcoin transactions.
Money for OS X/iDevices is pretty great in my opinion. It helps you take care of budgets, scheduled payments, and generates some nice reports based on your criteria.