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 mid-2017, I sold my San Francisco rental property for 30X annual gross rent and reinvested $500,000 of the proceeds in real estate crowdfunding through RealtyShares. With the new tax policy in 2018 and beyond capping state income and property tax deductions to $10,000 and limiting interest deduction on mortgages of only $750,000 from $1,000,000, expensive coastal city real estate markets should soften at the expense of non-coastal city real estate.
An obvious example is over exposure to bank stocks, which have been excellent investments for over a century.  Though a foundation of most portfolios, bank stocks do involve more risk at certain stages of the economic cycle than many realise.  Being less exposed to bank shares in the last few months could have preserved some capital.  So, a more diversified approach can help mitigate some of these risks.
It is very important to understand that contacting a “professional” to learn how to do this only results in them trying to sell me crap properties (whether high end or low end). I’ve tried contacting realtors out of state, and they attempt to sell me crap or someone else’s problem. No one has a vested interest in actually helping someone or teaching them about how to get an out of state rental. very frustrating. I could go out tomorrow and buy a rental in my city, but that is the last place I want to own one. Anyone? Are there an real people on here?
Since I knew I’d eventually be losing my day job income, I had to set realistic goals. There was no way I was going to make a six figure salary blogging and working online after only 2 years but I thought it might be possible to cover our monthly expenses for a few months while I took time off and looked for a new job. I already had some secondary sources of income and there were others that I specifically tried to build up.

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That's odd, because lot of these questions are actually pretty easy to answer. The IRS is good about publishing the data. Given that – and given the recent interest in personal income inequality, I decided to write a little bit about the different kinds of income people report on their tax returns. A longer paper – Sources of Personal Income – is here, but for a brief overview, you might want to check out the top ten sources of income:
I own several rental properties in the mid west and I live in CA. I have never even seen them in person. With good property management in place (not easy to find but possible) it is definitely possible to own cash flowing properties across the country. Not for everyone and not without it’s drawbacks, but it seems to be working for me so far. I’m happy to answer any questions about my experience with this type of investing.
An obvious example is over exposure to bank stocks, which have been excellent investments for over a century.  Though a foundation of most portfolios, bank stocks do involve more risk at certain stages of the economic cycle than many realise.  Being less exposed to bank shares in the last few months could have preserved some capital.  So, a more diversified approach can help mitigate some of these risks.

Here’s the truth: a successful business is something that successfully solves a problem. And that business can make more money in two ways: solving more people’s problems, or solving bigger problems. The cool thing about the EP Model is that sometimes these products don’t even have to be yours. You can generate income by recommending other people’s or companies’ services or products. This is called affiliate marketing. It’s actually how I’ve made most of my money since I started in 2008.
However, under certain circumstances, payment for personal services performed in the United States is not considered income from sources within the United States. For example, personal services performed by an independent nonresident alien contractor specifically exempted by a tax treaty. For more examples, see the Pay for Personal Service section in Publication 515, Withholding of Tax on Nonresident Aliens and Foreign Entities.
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