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Welcome to the WINDERMERE blog

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I talked with a client this week about the various social security claiming strategies. It’s an important question for everyone to consider so let’s take a closer look. Social security is a US federal insurance program funded by payroll taxes. It provides guaranteed, inflation-adjusted monthly income to eligible retirees, as well as disabled workers and […]

Client Question – Claiming Social Security

July 22, 2026

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There are certain questions I receive quite frequently given my profession. One of the most popular goes something like this “So, I read an article that the market is going to crash in the next year. What do you think I should do?” I had someone ask this question again recently and thought it was […]

Client Question: When Does “This” End?

July 14, 2026

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I talked with two clients this week about the pros/cons of funding purchases. I wrote about a similar topic a little while ago (the decision to finance or pay cash here). This time, the questions center more around what type of account to pull cash from – a pre-tax retirement account or a non-retirement/brokerage account. […]

Client Question: Funding a Purchase

July 7, 2026

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This week’s question came to me from a client who was in the market for a new car and asked for some advice. After a very lengthy discussion about car financing and negotiating (I LOVE this topic so I had a lot to say, as always haha!), she asked a final question. If I have […]

Client Question: Finance or Pay Cash?

May 28, 2026

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There are countless rules and regulations to keep track of in the world of investing. One of those items are the various account types and the associated rules and technicalities for each. By the time you reach a certain age and/or level of savings, you are very likely to have several unique accounts which might […]

Client Question: Accessing IRAs

May 13, 2026

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I received two questions about health savings accounts (here’s a prior post on the account basics) These are powerful accounts – both for near-term health spending or as an added tax advantaged savings account – so let’s look at the questions that arose. Eligible Expenses If you are able, it is a wise move to […]

Client Question: Health Savings Accounts

May 7, 2026

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A client took the quiz in last week’s newsletter (related to retirement savings accounts) and had a question regarding one of the answers. The question was an “all of the above” answers are true related to Roth vs traditional IRA accounts. Here was the statement he was questioning “Workers who want to contribute the maximum […]

Client Question: “To Roth or Not to Roth, That is the Question”

April 30, 2026

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If you actively managed your own investment portfolio (or a portion of it), odds are you’ve wrestled with this question at some point. I talked with a few clients this week about sell decisions (with various characteristics) and wanted to cover some of the highlights here Evaluate Reason to Sell Before taking any action, first […]

Client Question: When to Sell/Trim

April 23, 2026

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If you have a negative reaction to any form of debt, you are certainly not alone. And I would argue this automatic reaction is usually more favorable than the opposite inclination to take on debt at any price and in any situation (danger!) However, there can be certain instances where debt is a useful tool […]

Client Question: Home Equity Lines

April 9, 2026

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As an adult, there are a few things that never seem to reach an end but rather continue on an indefinite loop. Can we all agree that taxes are one of those things? A client recently finished their 2025 taxes and immediately had questions regarding what needs to be done for 2026. Honestly, it’s an […]

Client Question: Taxes are done, now what?

March 26, 2026

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