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Welcome to the WINDERMERE blog

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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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Markets are a bit jittery as of late which can translate into jittery investors. I talked to a client this week that was a bit concerned about markets and the potential impact a “market downturn” would have on his portfolio. It ended up being a useful discussion about how to frame asset allocation in terms […]

Client Question: Asset Allocation & Time

February 26, 2026

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I talked with a client last week about something he had overheard in a social situation. He thought it had to do with the need to live in a home for a certain number of years to avoid taxation upon sale – but he wasn’t sure of the specifics. This comment surely dealt with the […]

Client Question: Primary Home Sale – Capital Gains

February 19, 2026

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Ever since 2020, short-term rates have been rather favorable for investors in comparison to history (remember when money market funds paid over 5% – the good old days!) As the effects on the pandemic have subsided on many fronts, the fed funds rate has steadily declined and has taken the market rates on cash savings […]

Client Question: Cash Savings

January 28, 2026

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There are certain terms we all hear in the financial press each day that we may not fully understand. A client was wise enough to ask for clarification on one such term – index funds. Let’s take a look (one word at a time) What is an index? An index is a collection of specific […]

Client Question: Index Funds

January 21, 2026

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