For example, something like a home office deduction might impact your depreciation schedule or your qualified business income deduction.

Over the years, I’ve noticed something interesting working with investors:The biggest tax mistakes usually don’t come from shady strategies or bad CPAs…They come from poor recordkeeping and timing.Here’s what I mean A lot of investors don’t track which expenses are repairs (deduct now) and which are improvements (depreciate later).They toss all the receipts into a box or an app and hope it sorts itself out in March.Then when tax season hits, they realize half of those costs could’ve been handled differently — maybe deducted sooner or even structured better if they’d planned a few months ahead.The IRS doesn’t just care what you spent… it cares how you report it.

You are getting a depreciation deduction on someone else’s money.

You can absolutely deduct what you pay them, but it has to be treated as true interest, not a profit-share.

That means more cash flow, faster pay-back, and smarter reinvestment.What Is Cost Segregation & Why STRs BenefitCost segregation is the process of breaking down a property’s purchase price (or renovation cost) and reallocating portions of it into shorter depreciation lives (typically 5, 7, 15 years) instead of being lumped into the standard residential/structure life (27.5 or 39 years).For STRs (especially where average guest stays are short and you materially participate) this becomes even more powerful:It accelerates write-offs and frees up cash sooner.It helps you convert your property into an “active business” rather than passive income in the eyes of the IRS, making more deductions usable against other income.Personally I'm a realtor which makes it easy to gain "material participation" as I am classified as a "real estate professional"There are ways to structure a property that is managed by someone else and still qualify.

If the property qualifies as a separate activity, you may be eligible to claim bonus depreciation through a cost segregation study, which can provide substantial upfront deductions — particularly beneficial if you are in a higher tax bracket.However, if your income level is lower, the cost of the study may outweigh the benefit.

Vacation homes have limited deductions for expenses and depreciation, so converting to a full rental lets you take full advantage of those deductions.I’m assuming you’re also referring to the pass-through deduction.

If you take money from stock gain or crypto you will pay taxes on it- as mentioned you may get some deductions from real estate but it's deferred down the line 

And that’s usually where the biggest tax mistakes and missed deductions live.So when you’re evaluating CPAs, I’d recommend making sure you find someone who will actually push you to get proper bookkeeping systems in place — not just someone who files the return.

I had a huge amount of expenses in 2022- pool, new windows and doors, that I was unable to use as deductions because of my W2 income.