Congratulations on your tremendous income! You have worked hard and come a long way, and you should be very proud of that.
I am also not going to criticize you about the tithe and providing a helping hand to other family members. I think generosity of spirit is a trait to be admired, and as long as you understand and are willing to accept the consequences, then that is a reasonable choice to make.
But there are two mental shifts to make if you want to translate your high-income into long-term wealth.
The first is to understand that life is an "or," not an "and." Even someone with your tremendous income cannot afford a big house and a money-losing rental house and a cushy lifestyle for you and your kids and thousands of dollars a month for the church and religious school and helping family AND retire in 10-15 years. I think for many of us who came from more humble backgrounds, it is easy to think that an income like yours means you're rich and can have everything you want; you grow up with this vision of what "rich" means, and you start making more money than you ever dreamed, and so you assume that now you can live like that, and then 10 years later you wonder where the heck all that money went. The reality is that even people at your income level cannot have it all; the illusion that rich = big houses and nice cars and fancy clothes is just that -- an illusion created by advertisers who are falling over themselves to convince you to spend more of your money on stuff you don't need.
So what you need to do is really think about what your priorities are, and then decide whether you are deploying your money in the way that best gets you there. One way of thinking about it is that whatever you spend in a given year, you need to have 25x that amount invested to support that spending forever. So, for example, your cleaning costs you $320/mo, or almost $4K/yr; that means that if you want to keep this cleaning service forever, you will need to have almost $100K invested, just for that one thing. So in other words, your total 401(k) now covers your cleaning service and your clothes purchases, and nothing else. And that rental, with your @$600/mo loss without even considering vacancy or maintenance expenses? You'll need $180K extra saved just for the privilege of continuing to own it. That's over half a year's gross pay! Are you willing to work an extra 9-12 months just to continue to own and rent that house?
I would suggest doing this analysis in conjunction with this:
https://www.mrmoneymustache.com/2012/01/13/the-shockingly-simple-math-behind-early-retirement. Because every dollar you spend on stuff now is another dollar that takes you further away from retirement. So if you want to retire in say 15 years, you're going to need to save over half your salary. Which goes back to how "rich" you really are: you are living the lifestyle of someone who makes almost $300K/yr. But if you actually want to retire on a reasonable timeline, you can really only "afford" the lifestyle of someone who makes less than $150K/yr -- which is still very very generous!! You need to decide how much of that vast income you want to put towards Current You, and how much you want to put aside so that Future You will have the freedom to do whatever the heck she wants.
The second mindset change you need is more directed at your husband: he seems to be operating out of a sense of fear/insecurity, holding on to a property that by all accounts is losing you vast sums of money, and refusing to invest that money in the stock market, where you will make significantly more over the long term. Again, I think that is a natural response for people who did not grow up in abundance and have had to work for everything; when you can finally get something tangible, it feels real and safe. But that mindset is holding you back; you can see now from the numbers that instead of that property supporting you, you are working to support it! It has gone from a haven, from a symbol of success, to an albatross. So in his effort to be safe, he is hanging on to a property that is actually making you significantly
less safe every year, because it is draining your finances!
Unfortunately, he's not the one who wrote in asking for advice. ;-) So you are going to need to figure out how to persuade him. Maybe he needs to learn more about the stock market to feel more comfortable investing. Or maybe he's just not willing to let go of the need for something tangible. In that case, let him focus on real estate investing, but approach it as an actual real estate investor would, looking at the numbers to figure out what makes a good rental vs. a bad one. And that's the key: a real estate investor does
not buy property hoping that its value will go up -- that's speculation, not investing. A real estate investor buys property because it provides a good, positive net monthly cash flow -- meaning it brings in more than it costs, even including planning for vacancies and covering needed repairs and periodic upgrades. If the property value increases, that's just a bonus. Real estate investing may satisfy his need to have a tangible thing, while doing it the right way would help your budget instead of hurt it.
