Goals to get out of W2: need ideas

Thank you for sharing your story—it’s inspiring and incredibly relatable. Transitioning from a career in teaching to full-time real estate and entrepreneurship is a bold but thoughtful move, especially given your desire to prioritize your family and create more flexibility. It’s clear you’ve already laid a strong foundation by securing two STRs and self-managing them with a plan in place. While the cleaning work offers immediate savings, it may not be sustainable long-term with young children, adoption plans, and aging parents in the mix. Recognizing early that you can’t do it all is actually a strength—not a weakness—and will serve you well as a business owner.

In terms of replacing your $60K teaching salary, it sounds like you're well on your way, especially if your STRs perform moderately well. The real estate professional tax status is a powerful tool to help reduce taxable income, especially if your husband has a high W-2 income. That said, cash flow matters too, and it's wise to supplement STR income with something more predictable, especially early on. One path forward is to build a business around hospitality services in your area. Given the lack of STR-specific cleaners and your high standards, creating a premium vacation rental turnover and hospitality service could fill a niche. You already understand the needs of both guests and owners and could eventually hire and train others to handle operations. Think beyond just cleaning—offer package delivery prep, staging, small restocking, or even linen rental for STR owners. Market it as a "boutique STR support company" and emphasize your hands-on experience.

Another route some people take is STR co-hosting or property management, where you assist other investors in managing bookings, communications, and turnovers in exchange for a percentage of revenue. Many out-of-state investors are willing to give up 15–30% of their gross income for someone reliable to manage the day-to-day. Since you're already the boots on the ground for your own rentals, this could be a natural extension. Over time, you could scale this with systems and local help.

Also, don't underestimate the power of digital products or consulting. As a former educator, you're uniquely equipped to teach others what you're learning—whether it's how to manage STRs, how to vet and hire STR cleaners, or how to transition from teaching into entrepreneurship. You could develop a course, e-book, or even offer one-on-one coaching for teachers or parents looking to follow a similar path. Many people wish someone would walk them through that transition.

Ultimately, the advice I’d offer is to focus on scalability and flexibility. The cleaning business works, but only if you can systematize and eventually delegate. Look for income streams that don’t require you to be physically present for every dollar earned. You're already doing many things right—stepping into action, learning quickly, and recognizing the need for sustainable systems. Be intentional about each new commitment and build around the life you want to lead, not just the income you want to replace. You’ve got a powerful mix of experience, vision, and motivation to make it happen.