I hooked up all bank accounts, retirement accounts and credit card to Personal Capital. This aggregates everything into one centralized location and has fantastic visualizations that help track income, expenses, monthly cash flows and net worth. Once you've saved a little cash and start investing via a 401K plan through your W2 job or your personally opened IRA plan, there are some really great tools/visuals for retirement planning and asset allocation. If you go the rental property route, I have been using Stessa and it's been simple, easy to use and very helpful thus far in managing my property cash flow.
Lastly, it takes a ton of discipline for this, but I use my credit card for every expense possible during the month and then pay the full balance every statement. Get a good reward card (Chase Sapphire, CapOne Venture, airline one, etc) and the points accrue quite rapidly. My wife and I have taken numerous free trips as a result.