Hello from the Northwoods in Wisconsin! · 🏠 Lower Taxes w/ Ryan

Hello from the Northwoods in Wisconsin!

Hi Everyone, I own and manage a 5-star STR in northern Wisconsin in a resort area. I've been following Ryan and his team since the beginning of my journey. We aren't the typical Ryan Bakke follower... My husband and I left our high-paying jobs to move to the Northwoods to buy and run a resort, but when we couldn't find any that fit our wheelhouse, we switched to lake properties. That was also a struggle as many aren't built to our standards. But we did find one we liked, and after closing, spent 18 months renovating it. We did most of the work ourselves (I'm a creative and my husband is in construction). I currently manage the bookings, cleanings, marketing, guest communication... my husband helps with turnovers and maintenance.

We are about 85% direct and booked nearly 100% from the beginning of June through the end of August. Fall is usually 50% occupancy, but the other times (spring & winter) are very low. We have not found another property that cash flows.

Since then we've started a caretaking business, a mobile sauna business, and some remodeling/design work to make ends meet. In January my husband took a full-time job to supplement our income. We're about to purchase a local business, likely by the end of the year, that we'll both work at. This is will our main source of income.

We have not had good luck with tax preparers/CPAs, even though I thought I was asking all the right questions in the beginning. This year, because of what I learned from Ryan and his team, we amended our 21 and 22 taxes, and 23 & 24 are being finalized as we speak. We hired a capable bookkeeper and I got our current CPA to file Schedule E and reclassify some of our capital investments into shorter lives. I've spent countless hours learning about all of this to the best of my abilities (I'm a creative, so no small task!) and feel good about our progress.

But now we're moving into a potentially much higher income bracket and we're ready to really lean in even more!

Why do you want to save money on taxes? Not just “to save money” — but what does that money mean for your life? ••• We want entrepreneurship to look doable to our child (vs. really hard, which is how it appears right now). We want to live in a nice house again. We want to travel regularly.
Where are you right now in your journey? Just starting out? Own rentals? Flipping or doing STRs? ••• See above.
What’s your #1 challenge right now — your “big domino”? The one thing that would make everything else easier? ••• Finding an operator. We're in a resort area, so oversaturated with vacation rentals and lacking capable, trustworthy help. I would like to hand over the reins, but keep the total 5-star experience, something that currently sets us apart from our competition.

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