Unless you’re extremely disciplined and financially prepared, I’d stick with your current withholding strategy.

pretty standard for sellers that want post closing possession.what many do is withhold 5 to 10k and if they are not out by a certain date they lose it. that works. but if they have no money then..

@James McGovern I think you can reasonably demand they fill out a w-9 and if they won't with hold payment.

There are some where’s there’s a large penalty (call it 3X) if you withhold and the tenant wins in court. 

Sounds like you’re navigating a big transition and doing a lot of things right already by planning ahead and speaking with a tax attorneyA few things to consider or ask about when you meet with themCapital Gains Exemption If this was your primary residence for 2 of the past 5 years you may qualify for the Section 121 exclusion which allows you to exclude up to 250K in gains if single or 500K if married filing jointlyCapital Gains Bracket You’re right to look at your taxable income including W2 wages and life insurance proceeds to see where you land The life insurance death benefit itself is generally not taxable but if any of it was interest income it might be Ask the attorney to confirm that partEstimated Taxes If you sell the house and owe tax you may need to make an estimated payment to avoid penalties especially if your W2 job didn’t withhold enough for the yearHealth Insurance and Marketplace Credits Since you’re planning to go on your partner’s plan this may not apply but if for any reason you do end up looking at Marketplace insurance your income level will impact subsidies Ask how your income mix affects thisNew Business Planning Talk about how startup costs might be deducted how to structure the business (LLC S corp etc) and whether making a clean break this year or early next year gives you any tax advantageRetirement Account Planning If you have any traditional retirement accounts and this is a low-income year you might consider a Roth conversion or some other strategy to optimize your tax bracketIt’s totally normal to feel nervous about a big change like this but you’re already doing the most important thing which is planning proactivelyHappy to talk more if you want help organizing the numbers or figuring out what to ask I work with a lot of people going through life and business transitions like this and it’s all about getting the right pieces in place ahead of time

A listing agent refusing an inspection or withholding the report unless you have an agent is unusual, especially after just 2 days on market.

Please be aware, depending on how the contract was drafted, they may try to cure the defect in the property or have some grounds to withhold some parts of the money for any fees or expenses thus far.Note: This information is for educational and informational purposes only and does not constitute legal, tax, financial, or investment advice.

I’ve been hearing the same from a few experienced investors: speed is everything, especially with holding costs stacking up.

Tenants cannot withhold their payments or cancel a payment that has already been submitted.Ensure that you issue the appropriate notices and maintain thorough records of all communication, along with a detailed timeline of the situation.

If you become a nonresident alien, the Section 121 exclusion may no longer apply, and FIRPTA withholding (15%) could apply at closing.Lower 2025 Income: If you expect to earn less in 2025 (due to your job loss), selling in that year could place you in a lower tax bracket and reduce the effective capital gains rate.Installment Sale Option: You could consider selling via an installment agreement (if the buyer agrees), which spreads out the capital gains tax over multiple years, especially helpful if you're expecting lower income moving forward.Rental Conversion Strategy: Some people convert their home to a rental first, but this may not benefit you since the property is already eligible for the exclusion.