New member from Fairfax, VA

[John Pak]

Hello, my wife and I are about 10 years from retirement from our full-time jobs.  Our real estate goal is buy-and-hold rentals to provide partial income replacement upon retirement.

We currently live in a SFH with good equity and have 2 rentals, a townhouse and SFH, all in Fairfax, VA. We are looking to buy one or two more houses this spring/summer. We are working with a buyer's agent.

I joined BiggerPockets because I am starting to have questions about real estate that seem bigger than my experience thus far and don't seem to have a clear-cut "right answer."  After 11 years as a landlord, I am faced with issues that I weren't on my radar when I was just starting out-- what to do when a buy-and-hold investor has an excellent rental that needs major upgrades (roof, windows, kitchen, flooring); is it smart to covert to a rental a primary residence with lots of capital gains (and lose capital gains exclusion of primary residence); do you ever sell/1031 exchange a good-renting property for tax reasons and how do you figure that out; pull money out of a rental property with lots of equity or enjoy the cash flow?  

Thanks.  I will be busy reading up on the posts of interest, and if I can't find the answer to what I am looking for, I will post a question.  

[Young Moon]

John - as to your question about converting a primary to a rental, why not sell the primary and capture the gains tax free?  If you are married, this means you could capture 500k in gains and not pay any taxes on that.  You could then use the proceeds to either buy a similar property to rent out (which would be essentially the same as just converting your primary to a rental, but with a better tax situation) or do with that money as you wish, including paying down any existing properties (which could help you help with your cash flow, if you pay a property or two off).  Only drawback are the closing costs, but if your capital gains are significant, could be worth it.  I am not an accountant, so please don't take this as tax advice, but this could be something worth looking into.