I have to echo @Terrell Garren here. I did my first flip when I was 30. I waited until I was 39 to start investing in rentals. Yes, I was doing other things, yes they were important, but I wish I had started earlier. That is my main regret in this business, and I would say my only significant regret.
I rent out apartments in the C-D range in the nicest parts of rough urban neighborhoods. I self-manage those apartments, and I also do most of the maintenance and upkeep. My tenants have my cell phone number. You might call me a slumlord, but the police certainly don't. They call me an example of the kind of affordable-housing landlord that is part of the solution to the housing problems of the urban ghetto.
I won't tell you how much I have invested in real estate. That would be idiotic on a forum like this one. But I do have $33,000 in a legacy rollover IRA that a certified financial planner invests for me, and I will tell you that I think of that money as peanuts when it comes to retirement income, as any reasonable person should.
All the people I am still in touch with from high school and college have, at best, two nice cars, a nice home, a stack of monthly bills a mile high, family photos take by professionals, and money saved up in a 401K. I went to an unreasonable upscale suburban high school and hung out with smart people so a few of my old friends are now well-paid professionals, some married well, but the pattern is always the same. Two started businesses that eventually failed and went back to the corporate world, but that's it.
This year, my $33K, invested in mutual funds and ETFs, has remained $33K. I haven't made a penny on that money. My financial planner sweats bullets every time I talk to him, reassuring me that the market is going to go up, up, up, that this is wise investing for the future, that everything is fine.
That guy drives a BMW, lives in a half-million dollar house out in the sticks, and really likes glen plaid suits, double cuffs with cufflinks, and the kind of overly stylish business footwear that I refer to as "clown shoes." He is well aware that he is really failing in managing the test money I've invested with him. When I first met him, I asked him a simple question I got off real estate records: why did he sell a $170,000 house in a nice neighborhood and move to his $500,000 house in the sticks two years before?
His answer was telling: after hemming and hawing a bit, he explained it was so that his kids could have a nice backyard, truly the most ludicrous explanation of why it was necessary to take a $300,000 mortgage that I've ever heard. He then insisted, in a slightly shrill tone, that, "I am NOT house poor!"
I am just curious, at this stage, to see if he's going to make me ANY money by December. If not, I'll move the money elsewhere. This guy is at the absolute mercy of the markets. Sooner or later, when the business cycle turns, he's going to see a lot of the money under his management go bye-bye. It's as inevitable as the next sunrise. When that happens, my financial planner's going to get hammered. His high expenses will keep rolling along nicely, but his income will take a high-dive belly flop.
My financial planner, and my friends, are all in the same boat. They are one or two crises away from an economic bust. The people that I am friends with are all married, and their spouses work. Anything happens with their spouse or their spouse's job? Bust. Any health problems? Bust. Job loss? Bust. Any other major economic upheaval in their lives? Bust.
And every day, they log into their online accounts, look at their 401K, and hope they made money and didn't lose it that day. They will vote for any idiot who promises them that under their administration, the stock market will go through the roof.
Some of my friends are going to be working at Starbucks or McDonalds in their early sixties. That's statistically unavoidable. The bust will happen. The 401K will drop in value, The numbers won't add up, and the despair will set in. The American Dream will prove to be a lie for them.
But that's not what I worry about for my future.
I worry that someday, someone close to me is going to come and tell me that their child needs medical care that isn't covered under their medical insurance, and I won't have enough money to write a check for them. I think that the charity that I intend to endow in the future won't get enough to really do what I think it can do as a well-funded charity if I stop doing what I do now. I worry that someday, some deranged neo-Nazi party in the country of my birth may gain enough power to do real damage and I wouldn't be able to put any financial muscle behind organizations that will work to do something about it.
Convince your wife to get into this, Joseph. It's actually pretty difficult to screw up royally if you do your best to look ahead, make conservative estimates, aren't afraid to get your hands dirty, and keep your ego small and manageable. No, this is not an easy business. But it beats the pants off a cubicle and an online 401K account that you just hope doesn't lose any money today. There's a learning curve. So start small. Learn steadily. Work much harder than you expect for at least the first 10 years. It will get better.