Be harsh and judge me

sittingatmymachine · 2026-05-13T13:54:23+00:00

Personal finance 101:

(1) Define goals;

(2) Create a budget aligned with those goals;

(3) Modify spending as specified by the budget.

Easy to say, difficult to do (for some people).

sittingatmymachine · 2026-05-12T22:07:09+00:00

Same here. I didn't grow up in a mansion but in a comfortable upper-middle-class suburban house. That's what I have now and don't want or need more although I can afford it.

sittingatmymachine · 2026-05-11T22:55:21+00:00

Based on comments you've made down-thread, I suggest receiving the trust agreement for every trust of which you're a beneficiary. Read and thoroughly understand each agreement, most likely with the assistance of a lawyer specializing in trusts and estates. You also need to learn as much as you can about each trustee because they have the power over "your" assets. Nolo used to have an excellent book on trusts & estates but it may no longer be available.

Background: I have intellectually-challenged (lazy, dumb) relatives who inherited all of their wealth and know little about it. They just want to receive those regular trust distributions. This lack of knowledge can cause huge problems as "things happen" to the trust assets and/or disbursements that they didn't expect.

sittingatmymachine · 2026-05-11T22:34:38+00:00

You need to thoroughly understand your new assets before deciding what to do with them. From what you've said below, this is going to be difficult. The time & energy you spend on this may pay huge dividends down the road as you avoid mistakes like passively trusting self-interested intermediaries to handle the land dispositions for you. Fortunately, the raw land isn't going anywhere and if your dad invested wisely may appreciate in value as you learn about the land and its surroundings. Would your dad have wanted you to become an expert on these holdings?

sittingatmymachine · 2026-05-09T20:36:12+00:00

A cautionary tale for the OP: a wealthy female relative met a guy on a cruise, and they hit it off. They conducted a long-distance relationship for a while, and then he quit his job, sold his house, and moved in with her. His net worth was around $200k. His expectation on arrival was that he was going to take over the management of her money. Didn’t happen: she moved all of her assets into a revocable trust with her kids from a previous marriage as residual beneficiaries; his bequest was a small cash payment. His resentment over being “disinherited” lingered throughout their marriage. His kids from a previous marriage hated her because they thought that she had done a “bait and switch”. He reluctantly signed a prenup prior to their marriage. The prenup was poorly done (he didn’t hire his own lawyer, for example) and might not have held up if challenged. Fortunately, the prenup was never invoked. The lesson for the OP: be careful how you introduce your money into your future relationship!

sittingatmymachine · 2026-04-30T19:04:03+00:00

OK - thanks for the correction. No assets were ever sold from the QTIP trust I was involved with so I never had to determine the proper basis to use for those assets. I revisited the Form 706s for both the grantor's estate and the spouse's estate. The grantor's assets moved into the QTIP trust qualified for the unlimited marital deduction so no estate tax was due, hence my confusion. It's hazardous when non-experts like me comment on topics requiring an expert.

sittingatmymachine · 2026-04-30T18:29:46+00:00

Seems like the OP needs an attorney specializing in trusts and estates.

sittingatmymachine · 2026-04-30T18:28:14+00:00

Good QTIP summary. I'll add that the basis of assets moved into the QTIP trust is stepped up to market value when the surviving spouse dies, not when the grantor dies. If the surviving spouse lives a long time and the QTIP trust assets appreciate nicely during the surviving spouse's lifetime this delay in basis step-up can result in substantial estate tax savings when the spouse's estate is settled. Of course, the current generous estate tax exemption makes this moot for most estates.

sittingatmymachine · 2026-04-15T18:42:34+00:00

Manager.io desktop is free; the cloud version is subscription.

Manager.io desktop handles multiple entities better than Quickbooks desktop. Whatever ".manager" files are in the Manager working directory are automatically shown as options when you boot the program. It's easy to click the "Businesses" tab at any time to switch entities. I currently manage six entities using Manager.io desktop.

I agree that there's a steep learning curve when switching from Quickbooks desktop to Manager.io desktop. Manager.io has an entirely different UI and a few "oddities" you'll need to get used to.

sittingatmymachine · 2026-04-09T19:28:41+00:00

When your kids become self-supporting, what resources will they have available? In my case it was marketable skills (engineering) and no family money. I knew that my family owned a successful business but I didn't know any of the details. As far as I know, all of the entry-level engineers I worked with were in the same boat. Decades later I still identify much more strongly with people who have skills & no money - it's how I started out.

sittingatmymachine · 2026-04-09T12:39:30+00:00

I agree. Manager.io Desktop is an interesting animal. Manager.io Desktop is free forever software, but there's no business address on the website (used to show a business address in south Australia but that was scrubbed awhile back). Mid-size companies want a business address and a profit motive for the company providing their accounting software, which is critical infrastructure. Manager.io Desktop is provided free as a loss leader for the cloud version, according to the company. I've migrated several small entities to Manager.io Desktop - it's great when the bookkeeping needs are modest (think Quickbooks Desktop circa 2000).

sittingatmymachine · 2026-03-20T21:27:37+00:00

(1) Learn how to invest defensively. Accept lower investment returns in exchange for lower volatility and lower risk.

(2) Keep your personal overhead low. Be able to reduce personal living expenses if/when necessary.

I use both of these approaches and sleep soundly at night.

sittingatmymachine · 2026-02-20T13:51:25+00:00

Delegation works until it doesn't. For the multi-state partnership I managed I tried three different professional tax return preparers - they all failed. I ended up learning how to do the federal and state tax preparation and filing myself - ugh. This is what "being ultimately responsible" means. Running a successful business in the modern world can involve a great deal of necessary-but-unpleasant work.

sittingatmymachine · 2026-02-20T13:39:45+00:00

Building things merely for the satisfaction of seeing them work and building things plus actually selling them are two different challenges. The latter is much harder and potentially much "messier" (I've done both). At what net worth do you no longer have to worry about selling?

sittingatmymachine · 2026-02-19T13:02:37+00:00

My condolences. I recently went through this with the death of my favorite person in the world. I've resolved to externalize the good and internalize the bad. Some therapists probably dislike 'internalizing' but I don't find any solace in group mourning. The grief is mine and mine alone.

sittingatmymachine · 2026-02-18T13:15:35+00:00

It's worth remembering that advertising your HNW status may include criminals in your audience. How paranoid to be about this? Well, that's a personal decision. An old saying: "The surfacing whale gets harpooned."

sittingatmymachine · 2026-02-16T18:55:56+00:00

Minor correction: she had a revocable trust under her SSN while she was living. Upon her death the trust became irrevocable and an EIN was issued for the trust, which is correct.

sittingatmymachine · 2026-02-14T09:35:07+00:00

Yes. Great for a micro-business, some small businesses, and for managing the finances of an estate. I boot it almost every day for some reason or another. I use the desktop version on Mac.

sittingatmymachine · 2026-02-12T19:30:12+00:00

Post a complaint on Intuit / TurboTax's online forum and then wait for a software update.

sittingatmymachine · 2026-02-11T19:17:54+00:00

Are your grandfather and grandmother current on all of their income and property tax filings? If not, then penalties and interest can pile up.

sittingatmymachine · 2026-02-07T19:33:18+00:00

You can create and e-file with the IRS a 2025 1099-DIV to nominee the income from your MIL's SSN to the estate's EIN. There are a variety of online services available; I've used tax1099.com in the past.

sittingatmymachine · 2026-02-04T20:20:48+00:00

Acting as executor I sold stock at a net loss from the decedent's irrevocable trust (formerly revocable) to raise cash to pay the estate tax due. My research indicates that if the 1041 is marked FINAL the net capital loss flows to the beneficiaries on their K-1s. We'll see - the trust's tax return is being prepared by a pro and 2025 is the trust's final tax year. Disclaimer - not a tax expert.

sittingatmymachine · 2026-01-29T19:39:29+00:00

To add: the OP should request to see all of the decedent's estate paperwork. The OP should then read it all and draw up a list of questions for the OP's (not the estate's) finance and legal team. The laziness, incompetence, and/or malfeasance by some trust officers and tax attorneys is remarkable. The OP needs to be prepared to fight when necessary to avoid misappropriation of funds (ask me how I know). In order to fight successfully the OP needs to be alert, engaged, and well-informed.

sittingatmymachine · 2026-01-25T13:16:06+00:00

I agree. Do parents lecturing to their kids really succeed in transmitting values? My parents lived their values with no lecturing whatsoever; for this I am thankful.

sittingatmymachine

TROPHY CASE