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.
In the case of an activity with respect to which any deductions or credits are disallowed for a taxable year (the loss activity), the disallowed deductions are allocated among your activities for the next tax year in a manner that reasonably reflects the extent to which each activity continues the loss activity. The disallowed deductions or credits allocated to an activity under the preceding sentence are treated as deductions or credits from the activity for the next tax year. For more information, see Regulations section 1.469-1(f)(4).
Case Schiller only tracks price appreciation of RE. RE as rental investment vehicle is measured primarily on rental yield or cap rate or some other measure. Price appreciation in that scenario is only a secondary means of growth, and arguably should be ignored as a predictor of returns when deciding on whether or not to invest in rentals. More important key performance indicators for rentals are net operating income and cash ROI. Appreciation, if it occurs, is a bonus.
Passive income investments can make an investor's life easier in many ways, particularly when a hands-off approach is preferred. The four options outlined here represent differing levels of diversification and risk. As with any investment, it's important to weigh the anticipated returns associated with a passive income opportunity against the potential for loss.
Rentals, just like stocks, throw off cash. With rentals we call that cash “rent”, and with stocks we call it dividends. A significant difference however is that the S&P 500 has appreciated at ~6% per year (above inflation) for the last 100 years…..Real Estate has had almost 0 growth above inflation. So are rents higher than dividends? Maybe, maybe not. But unless you got one heck of a deal, the delta in rent over dividends will have a very tough time making up for the 6% per year difference in appreciation.

If you are too risk-averse to engage in stock trading, there’s a much safer option to earn passive income, albeit with much lower margins of return: certificates of deposit or fixed deposits issued by banks. These financial vehicles are similar to mini investments. CDs work very similar to savings accounts with one notable difference. Once you place a deposit, it cannot be withdrawn until the certificate matures. You can obtain these certificates for lump sums of cash that you can allow to mature within time periods like 2 years or 5 years. The advantage of CDs is that they offer higher interest rates than regular savings accounts. You can rest assured that the money will be safe in the bank. A CD earns interest quarterly or annually and all you have to do is just sit back and wait for it to mature.
Truebill is an app that helps you save money by identifying recurring subscriptions and other bills and helping you cut costs by negotiating better rates and fees. One of their partnerships is with Acradia Power, which has the potential to save you up to 30% on your electric bill. It searches for better power rates in areas where competition is allowed, and it locks in the better prices for you.
If any amount of your pro rata share of an S corporation's loss for the tax year is disallowed under the basis limitation, a ratable portion of your pro rata share of each item of deduction or loss of the S corporation is disallowed for the tax year. For this purpose, the ratable portion of an item of deduction or loss is the amount of such item multiplied by the fraction obtained by dividing:

If you like the “job” of wholesaling or flipping or landlording, or whatever it is you may be doing actively to earn income, rock on with it. Especially if you are using the income from that job to buy passive investments with, which is how one really becomes successful- find ways to fund buying passive investments that will lead you towards financial freedom. On that note too though, you can work any job or build a business to earn income that you can use to invest in passive investments. It doesn’t have to be flipping or wholesaling or landlording, albeit you do learn a lot about investing working those jobs, but it can be any job you want totally outside of real estate if you want it to be. Real estate is just a great way to earn some fat cash, which is why so many people stick with it. And if you do that, you are awesome still, as long as you realize you are working a job.
Income from an oil or gas property if you treated any loss from a working interest in the property for any tax year beginning after 1986 as a nonpassive loss, as discussed in item (2) under Activities That Aren’t Passive Activities , earlier. This also applies to income from other oil and gas property the basis of which is determined wholly or partly by the basis of the property in the preceding sentence.
Investing in a business: Another good way to generate passive income is to invest in a business --even a small one -- in return for a percentage of the profits - just like Shark Tank, only smaller. Lending $10,000 to a local business that, for example, is working on a mobile app for Apple phones could lead to a passive income-generated share of the profits when that mobile app starts selling like hot cakes.
Another great aspect of passive income is that it is often completely scalable. Consider my book. If I sell 10 copies of it, I might get $100. If I sell 100 copies of it, I might get $1000. How much additional work did it take for me to sell those extra 90 books? Zero. And there’s nothing keeping me from selling 1,000 or even 10,000 copies of the book. A website is the same way. No limit on the eyeballs that can view it (as long as I keep upgrading the hosting plan!) Shares of stock are the same way. Owning 100,000 shares is no more work than owning 10 shares. If you’re a real estate investor, once you get your “system” in place (agent, insurance guy, attorney, accountant, property manager, repairman etc) it may not take you much more work at all to own ten properties than to own one. Maybe you do speaking gigs and charge $50 a head. Is it any more work to speak to 500 instead of 50? Not really. Leveraging your money is great, but leveraging your time through scalability is even better.
​Self Publishing is mainstream today. When you purchase an eBook off of Amazon there’s a pretty good chance you’re buying a self-published book. Self-publishing is also ridiculously easy. I tried this a few years ago and couldn’t believe how simple the process was. To self-publish a book you’ll first need to write and edit it, create a cover, and then upload to a program such as Amazon’s Kindle Direct Publishing. Don’t expect instant success though. There will need to be a lot of upfront marketing before you can turn this into a passive income stream.
There are three main categories of income: active income, passive income and portfolio income. Passive income has been a relatively loosely used term in recent years. Colloquially, it’s been used to define money being earned regularly with little or no effort on the part of the person receiving it. Popular types of passive income include real estate, peer-to-peer (P2P) lending and dividend stocks. Proponents of earning passive income tend to be boosters of a work-from-home and be-your-own-boss professional lifestyle. The type of earnings people usually associate with this are gains on stocks, interest, retirement pay, lottery winnings, online work and capital gains. 
Active investors are those who operate their investment properties as a business. The majority of their annual earnings come from their rental properties and they spend 750 or more hours throughout the tax year operating the property as a business. Active investors are also termed “real estate professionals” by the IRS, since their rental property businesses are considered their primary occupation.

All ideas take some amount of time and money to come to fruition. Some people have a lot of one of these, but not much of the other. A lot of successful ideas have started when one person had the resources that another did not. And many businesses have been started using 0% loans from credit cards to fund their concept and keep the business going until it achieved success.

You are also free to choose a fund that is based on any index that you want. For example, there are index funds set up for just about every market sector there is — energy, precious metals, banking, emerging markets — you name it. All you have to do is decide that you want to participate, then contribute money and sit back and relax. Your stock portfolio will then be on automatic pilot.
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