Buy or inherit and hold all their lives while working the properties for income.I've seen teachers, firemen, software engineers and all sorts of people utilize both strategies successfully.

Looking for simple online payment software. 

Starting out with a property that you live in sounds like a good plan remember to research that investment carefully we make our money when we buy I recommend you purchase flip comp software to help you something that will bring you equity after closing to work on your next deal with.

Looking for new software to help manage my existing rentals.

Some homes use an automated schedule system and a lockbox.

If it breaks in 5 years and I have to replace it (as opposed to repairing it), then I have 5 years of reserve to assist in paying for it, and I take the capital loss on my tax return for the difference.It's not perfect but for me, it's easier than tracking everything down to a penny (I press the button to depreciate property for the month in my accounting software and I transfer the expense amount to a savings account for reserves).

We have a couple of investors who stay confused by our Property Management policies, when we pay, what we charge and do not even know how to use their PM software because they have 10 different PM's using multiple different PM software programs.

https://www.amazon.com/Quicken-Property-Personal-Budgeting-Software/dp/B01K4RAAD0/ref=sr_1_1?

As far as managing your own rentals- if you don't have any sort of software system in place, I would HIGHLY recommend Appfolio.

Does anyone in BP have recommendations for Tax Software they use for real estate investing and/or a referral for a CPA specializing in Real Estate located in the LA/Bay Areas?