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Welcome to the WINDERMERE blog

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When it comes to income taxes, there is no shortage of rules, acronyms, and best practices. One such “tax term” came up this week as I worked thru a retirement plan distribution for a client. Find out what “safe harbor” means in terms of estimated income tax payments and why it’s a strategy you should […]

Client Question: Safe Harbor

June 1, 2023

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Undoubtedly, our clients are free to do what they choose with their invested funds. However, it is not uncommon for them to seek my advice when it comes to withdrawals – especially those that are above and beyond their planned/recurring distributions. Taking funds out of savings runs contrary to what our actions have been most […]

Client Question: Evaluating Withdrawals

May 24, 2023

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I onboarded a new client this week, and within minutes of looking at his pre-existing Roth IRA and tax returns for the given years, I realized he had made improper contributions to his account (due to exceeding the income limit). While he had an advisor helping him, that individual did not confirm my new client’s […]

Client Question: Improper Roth Contribution

May 18, 2023

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In reviewing a portfolio with clients this week, we were discussing a particular holding that was under water (valued at less than they paid for it). We had a good discussion about how to approach positions in an unrealized loss status and I thought it would be worth sharing Investing in public markets is a […]

Client Question: Under water positions

May 4, 2023

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Every once in a while, I have a topic come up in multiple client conversations in a given week – and this week that happened with life insurance. I’m taking that as a sign that it’s a good time to cover a few considerations with this topic! Please note that I’m not going to address […]

Client Question: Life Insurance

April 27, 2023

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I was talking with a client this week about this “in between” time – the time after the mad dash of first quarter to-do’s (like tax prep and payment) and the easy-going summer months (when, let’s admit it, few of us want to focus on financial tasks!) She asked what she should be getting in […]

Client Question: Financial House Spring Cleaning

April 20, 2023

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If you are a procrastinator when it comes filing your income tax return, rest assured you are not alone. The IRS reported that it had received 90 million tax returns as of March 30th (of an estimated 168 million) so clearly, a lot of returns will be coming in under the wire! I’ve heard from […]

Client Question: Tax Deadlines

April 12, 2023

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We’re in the homestretch of the 2022 tax season and as a result, I’ve been fielding questions about IRA and Roth IRA funding. I recently helped a few clients contribute to Roth IRAs (despite being over the income limit) and thought it may be a useful item to touch on this week Wait, what’s a […]

Client Question: Roth IRA Funding

March 30, 2023

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There have been quite a few new terms floating around these days, given all the events concerning the banking industry. One of those terms is “cash sorting.” A client recently reached out to clarify what this terms means – and whether it was an activity they should undertake. Let’s take a closer look Why is […]

Client Question: Cash Sorting

March 22, 2023

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Given the events of the past week, it’s natural that people are reevaluating their own cash management strategies. Chief among the questions I heard from clients this week is whether their money is “safe” at the bank. Let’s review the basis of bank deposits and the potential guarantees of those funds. What happens to money […]

Client Question: FDIC Insurance

March 16, 2023


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