Anthony, nice setup! To your question about the rental mortgages, you haven’t said what interest rate you are paying. As a start, if you are paying more than the risk free rate (Treasury bills) which you probably are, then a true apples to apples comparison would be yes, pay off the mortgage. But, if you are comfortable taking more risk, you have other options to invest in which you *hope* will yield you more over the coming years. You also didn’t say whether the rentals generate net income and if so, how much? What is the implied rate of return on the equity you have invested in them? If you pay the mortgages off, you’ll have even more equity tied up, will the extra net income make that worthwhile? Maybe you should use the money to buy more rentals instead, if purchase opportunities still exist in your town. … this is less of an answer than a framework to analyze the decision, hope it is helpful.

Investing in bonds: Similarly, bonds are an attractive way to engage in passive income. Over a recent 45-year period, bonds funds, as measured by Vanguard Funds, returned 7.1%. Of course, there's no guarantee that investments in stocks or bonds will always work out well, investing in them is by far the surest way to generate money through passive income.
You may think of a savings account as just that, savings. But it’s actually another form of income as the money in the account will draw interest. And while this interest may be small, it’s still better than $0. Eventually, you can invest this money whenever an opportunity presents itself in order to gain other income streams.  Look into Tax Free Savings Accounts if you are going this route.
Investment in real estate can also be a source of a second income. If you have a decent sum of money lying around, you can use it to invest it to buy your second home. You may even take a home loan to finance your second home. This can become a source of income for you when you rent it to someone. These monthly rents would become your secondary monthly income. The key to making more money with rental properties lies in buying smart. Not all kind of property is going to give you a good return. Hence, analyzing the potential real estate opportunities is very important. The monthly rent highly depends on the area/location of the property hence it is highly important that you select the location of your property very wisely, keeping in mind the rent factor. You can save much even after your home loan EMIs. In addition to this, you can also avail tax exemption on the purchase of your property if it is through a home loan.
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I enjoy how you lay out real numbers. A lot of people wouldn’t do that. While you admit that you are somewhat conservative, I think the $1M in CD’s is just too conservative. Assuming you don’t need the cash flow now (which you say you just save anyways) then all that could be invested for potentially higher returns. For example, what if you bought San Francisco real estate along the way instead of CD’s. Or, an SP500 Index fund. I bet your average return would have been higher than 3.75%. Sure you could lose it, but the point is if you don’t need the cash flow now, you should try to increase that nut as high as possible until the day you actually need it. Your nut could be $5M right now if you had invested in asset classes other than CD’s for the last 14 years. Don’t get me wrong, you have done far better than me, but I guess I would take a little more risk if you don’t rely on that cash flow.
The rupee was linked to the British pound from 1927 to 1946, and then to the US dollar until 1975 through a fixed exchange rate. It was devalued in September 1975 and the system of fixed par rate was replaced with a basket of four major international currencies: the British pound, the US dollar, the Japanese yen and the Deutsche mark.[324] In 1991, after the collapse of its largest trading partner, the Soviet Union, India faced the major foreign exchange crisis and the rupee was devalued by around 19% in two stages on 1 and 2 July. In 1992, a Liberalized Exchange Rate Mechanism (LERMS) was introduced. Under LERMS, exporters had to surrender 40 percent of their foreign exchange earnings to the RBI at the RBI-determined exchange rate; the remaining 60% could be converted at the market-determined exchange rate. In 1994, the rupee was convertible on the current account, with some capital controls.[325]
For a person working for a wage, their source of income is their job, or their labor (aka their time that they sell to someone). But you can own a house, and rent it out, and when your renters pay you renter every month, the source of that income check is your rental property, or your house. It would just be called rental income. If you have money in the bank in an account that pays interest, those interest payments are another source of income. We can say the source is interest payments, or we can identify the asset that is generating rent, and say your money in the bank that is generating “rent” (aka interest) is your source of income.
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