Withholding with your employer only knows about the income that you earned with them.

@Barbara Johannsen  Hi Barbara,I’ve been involved with holding performing real estate notes for a while, and it’s definitely a different ballgame compared to traditional property investing.

The lease clearly says no alterations or improvements including changing or adding lock without my written approval, and tenants are responsible for any costs or damages from unauthorized changes.I’m very upset because they didn’t ask for my permission—this is my property—and I also feel uncomfortable with the  request for payment.I’m worried: if I don’t pay, they might withhold the key; if I do, they might demand more changes in the future.

Problems/errors on statements, lack of communication, withholding statements for over three months? 

Luckily, I took before and after photos/videos, so at least I have that documentation if she withholds it. 

Title has to also withhold proceeds for state taxes unless you say you are staying in Oregon.

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

If and when you go to court for an eviction or a tenant withholding rent due to maintenance issues, the first thing the judge is going to ask is going to be who your broker is.

Here’s what the law expects:Pay your rent—on time.Keep the unit clean and safe.Don’t damage the property or disturb others.Use appliances and utilities as intended.Give proper access when requested for inspections or repairs.Landlords must give 24 hours' notice to enter (except in emergencies), and they’re expected to be reasonable about timing.Now, if your landlord fails to fix serious issues (leaks, mold, no heat), here’s what you can do:Give written notice.Give 14 days to fix it.If they ignore it, you can break the lease or sue for damages.What you can’t do: withhold rent or make repairs and deduct the cost—unless you have written permission.And when your lease ends?

They are not legally allowed to withhold the entire rent.