My work is rather demanding so I don't have the time to dive in to Real Estate investing from a distance in my current career (maybe in 5-6 years when I'm retirement eligible).

The short-life stuff gets depreciated faster, so you front-load deductions.

Very cheap (only $480-$700/year) for me with a 5k deductible.

.✅ Did you know you don’t even have to be VA-eligible to assume a VA loan.

Quote from @Matthew Hamilton: There isn’t really a “penalty” for having the property as a rental for three years, but you may lose eligibility for the federal capital gain exclusion if you hold it too long.Here’s how it works:The IRS allows you to exclude up to $250,000 of gain if single or $500,000 if married filing jointly when selling your primary residence, as long as you’ve owned and lived in it for at least two of the five years leading up to the sale.Since you moved out in March 2023, you’d still meet that “2 out of 5 years” rule if you sell by March 2026.

What are the key things we need to be aware of as far as choosing the deductable?

If I wait until I become eligible to live off base, which is at least after three years of service for the Air Force, I could use the VA loan.

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.

Depending on your full situation, you could lose out on the QBI deduction if you go that route.

Your income affects the deductibility of the loss.