South Central Wisconsin · Member since 2025 · 16 posts · 10 votes
Hi everyone, I am new to investing. I have been a teacher of Family and Consumer Sciences to teenagers for the past 13 years. My husband talked to me forever about real estate investing and I was too stubborn to get in on it when we should have. But I've seen the light and have now jumped in with both feet. Long story short, we have two STRs that I will be officially posting this week. We are planning to self manage and I am going to be the "boots on the ground" for cleaning (due to a limited number of cleaners willing to do what I want for a vacation rental). We also have a 4 year old at home and are waiting to match for adopting a second child. As a teacher, I'm feeling burnt out and lacking the time to care for my family who has higher needs than typical. I am realizing that I cannot do it all. Therefore, I am either leaving teaching this year (17 more days) or next school year. What I'm struggling with is how I can find a way to replace my current salary of 60k. We accounted for the savings on hiring cleaners as well as the tax benefit of me being a real estate professional, but we would still like more so that we can continue scaling. The hope is to buy a third property this fall. I considered offering cleaning/hospitality services to other people in the area and creating a mini business with that, but I'm open to creative ideas to gain a flexible schedule with two young kids, aging parents and a business. What do other people do? Is there anything that you wish you had and I could offer to you or people in my area? Is there advice you have for me regarding any aspect of our situation?
Hi everyone, I am new to investing. I have been a teacher of Family and Consumer Sciences to teenagers for the past 13 years. My husband talked to me forever about real estate investing and I was too stubborn to get in on it when we should have. But I've seen the light and have now jumped in with both feet. Long story short, we have two STRs that I will be officially posting this week. We are planning to self manage and I am going to be the "boots on the ground" for cleaning (due to a limited number of cleaners willing to do what I want for a vacation rental). We also have a 4 year old at home and are waiting to match for adopting a second child. As a teacher, I'm feeling burnt out and lacking the time to care for my family who has higher needs than typical. I am realizing that I cannot do it all. Therefore, I am either leaving teaching this year (17 more days) or next school year. What I'm struggling with is how I can find a way to replace my current salary of 60k. We accounted for the savings on hiring cleaners as well as the tax benefit of me being a real estate professional, but we would still like more so that we can continue scaling. The hope is to buy a third property this fall. I considered offering cleaning/hospitality services to other people in the area and creating a mini business with that, but I'm open to creative ideas to gain a flexible schedule with two young kids, aging parents and a business. What do other people do? Is there anything that you wish you had and I could offer to you or people in my area? Is there advice you have for me regarding any aspect of our situation?
Hi Ashley!
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.
Note: This information is for educational and informational purposes only and does not constitute legal, tax, financial, or investment advice. No attorney-client, fiduciary, or professional relationship is established through this communication.
Have you considered raising capital from your network to help you buy more properties quicker? You could give enticing equity splits to create high upside for investors - this would allow you to scale quicker and make a portion of all profits. You can scale infinitely vs scaling when you have excess cash. You'd use the performance of your 2 STRs to show you can successfully run an STR.
Hi everyone, I am new to investing. I have been a teacher of Family and Consumer Sciences to teenagers for the past 13 years. My husband talked to me forever about real estate investing and I was too stubborn to get in on it when we should have. But I've seen the light and have now jumped in with both feet. Long story short, we have two STRs that I will be officially posting this week. We are planning to self manage and I am going to be the "boots on the ground" for cleaning (due to a limited number of cleaners willing to do what I want for a vacation rental). We also have a 4 year old at home and are waiting to match for adopting a second child. As a teacher, I'm feeling burnt out and lacking the time to care for my family who has higher needs than typical. I am realizing that I cannot do it all. Therefore, I am either leaving teaching this year (17 more days) or next school year. What I'm struggling with is how I can find a way to replace my current salary of 60k. We accounted for the savings on hiring cleaners as well as the tax benefit of me being a real estate professional, but we would still like more so that we can continue scaling. The hope is to buy a third property this fall. I considered offering cleaning/hospitality services to other people in the area and creating a mini business with that, but I'm open to creative ideas to gain a flexible schedule with two young kids, aging parents and a business. What do other people do? Is there anything that you wish you had and I could offer to you or people in my area? Is there advice you have for me regarding any aspect of our situation?
Hi Ashley!
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.
Note: This information is for educational and informational purposes only and does not constitute legal, tax, financial, or investment advice. No attorney-client, fiduciary, or professional relationship is established through this communication.
Rental Property Investor · WI · Member since 2023 · 192 posts · 143 votes
1y
Ashley, I hear where you are coming from. We are trying to do the same thing. I am an investor about an hour and a half east of you in Sheboygan. We are working to build up our cashflow to $11K per month. Hopefully after expenses it equates out to about $100K per year. Our strategy, while not quick, is to track what our cashflow would be with a portfolio that is completely paid off. We only have long term rentals. We started in the summer of 2021 and now have 6 properties 8 doors. If these properties were paid off our cashflow would be around $10,275 per month. My expectation is with rent increases over time this will grow to our goal of $11K. I plan on taking the next 6 years and paying all of these properties off, at which point we will be able to make enough off our portfolio for my wife and I to quit our current W2's. This would be great timing because our oldest would just be finishing high school. Similar to you my wife is thinking about starting up a cleaning business to add a little supplemental income. I also am thinking about working at the local golf course when I retire for some additional income. What I have learned is that this is totally doable in 7-10 years with a small and mighty portfolio depending on your lifestyle. I am also assuming you can make more in Madison then you can here in Sheboygan, and STR tends to make more profits then long term buy and hold. I wish you the best of luck!
Rental Property Investor · Somewhere over the Rainbow · Member since 2021 · 1k+ posts · 1k+ votes
1y
I'm in a similar position with my wife - high W2 for me, she's currently working full time, young kids - and trying to figure out a way to replace her income
REP is a must for the "non-working" spouse - the tax savings here make it worth it. Not only that, I think there's a lot of value that can be added in a supporting role - book keeping, general analyzation of property performance, possibly managing, finding deals.
Next I'd look to your husband possibly "hiring" you to work in the RE business. More deductions here if you're on payroll. I don't know too much about this option - but it may be worth it to meet with a tax strategist - not a CPA but a strategist.
Next, is acquiring customers (for whatever business) and getting a recurring revenue stream. This imo is necessary for scaling. If you start a cleaning business/yardwork etc - think about the exit. You'll need to train someone to take over the manual labor so you can step into a management role. You're aiming for time freedom here.
We've thought about social media - essentially the content guru route. Could offer lots of free info, gain a following then start charging for specialized information/strategies. May be able to monetize social media as well - this realistically will take several years for organic growth - would need to make videos, edit them etc. I think AI could be a big help here.
Not only do you have to replace the income - but also the benefits. Insurance? Retirement? Those are the other two we're currently trying to figure as well.
I'm in a similar position with my wife - high W2 for me, she's currently working full time, young kids - and trying to figure out a way to replace her income
REP is a must for the "non-working" spouse - the tax savings here make it worth it. Not only that, I think there's a lot of value that can be added in a supporting role - book keeping, general analyzation of property performance, possibly managing, finding deals.
Next I'd look to your husband possibly "hiring" you to work in the RE business. More deductions here if you're on payroll. I don't know too much about this option - but it may be worth it to meet with a tax strategist - not a CPA but a strategist.
Next, is acquiring customers (for whatever business) and getting a recurring revenue stream. This imo is necessary for scaling. If you start a cleaning business/yardwork etc - think about the exit. You'll need to train someone to take over the manual labor so you can step into a management role. You're aiming for time freedom here.
We've thought about social media - essentially the content guru route. Could offer lots of free info, gain a following then start charging for specialized information/strategies. May be able to monetize social media as well - this realistically will take several years for organic growth - would need to make videos, edit them etc. I think AI could be a big help here.
Not only do you have to replace the income - but also the benefits. Insurance? Retirement? Those are the other two we're currently trying to figure as well.
And inflation. $10k/mo today is $15k/mo in 12-15 years.
The right strategy is to keep your W2 reap the benefits-- cause there are plenty of those. Start planting the right seeds, let it mature, and change your perspective to enjoy the process. Perhaps 1 quality RE invest annually for 7-10 years, a small business that can support the RE business created in year 3-5, and other investments such as equities/debt. In a few years, restructure yourself with optimizing the properties by selling 2-3, eliminate debt, and keep performance better.
Phase yourself out of the W2 but do not quit and lose insurance, retirement, and then add kids in arguably the second most inflationary period we'll see in our lifetimes. You're going to be stuck.
I'm in a similar position with my wife - high W2 for me, she's currently working full time, young kids - and trying to figure out a way to replace her income
REP is a must for the "non-working" spouse - the tax savings here make it worth it. Not only that, I think there's a lot of value that can be added in a supporting role - book keeping, general analyzation of property performance, possibly managing, finding deals.
Next I'd look to your husband possibly "hiring" you to work in the RE business. More deductions here if you're on payroll. I don't know too much about this option - but it may be worth it to meet with a tax strategist - not a CPA but a strategist.
Next, is acquiring customers (for whatever business) and getting a recurring revenue stream. This imo is necessary for scaling. If you start a cleaning business/yardwork etc - think about the exit. You'll need to train someone to take over the manual labor so you can step into a management role. You're aiming for time freedom here.
We've thought about social media - essentially the content guru route. Could offer lots of free info, gain a following then start charging for specialized information/strategies. May be able to monetize social media as well - this realistically will take several years for organic growth - would need to make videos, edit them etc. I think AI could be a big help here.
Not only do you have to replace the income - but also the benefits. Insurance? Retirement? Those are the other two we're currently trying to figure as well.
And inflation. $10k/mo today is $15k/mo in 12-15 years.
The right strategy is to keep your W2 reap the benefits-- cause there are plenty of those. Start planting the right seeds, let it mature, and change your perspective to enjoy the process. Perhaps 1 quality RE invest annually for 7-10 years, a small business that can support the RE business created in year 3-5, and other investments such as equities/debt. In a few years, restructure yourself with optimizing the properties by selling 2-3, eliminate debt, and keep performance better.
Phase yourself out of the W2 but do not quit and lose insurance, retirement, and then add kids in arguably the second most inflationary period we'll see in our lifetimes. You're going to be stuck.
Ah - you put it exactly into words. I've been realizing that exact process as time passes. Initially you think (due to social media) that you can buy a few rentals and retire on the "cashflow". Quickly, you realize you'd need a lot of houses, the cashflow isn't all that great (after expenses/management) etc. BUT there's long term benefits in taxes, appreciation and loan paydown - so instead of going "all-in" it makes more sense to diversify your portfolio w/ RE.
But you still need cashflow - this is where the business comes in. Business cashflow. So you start a business or buy an existing one.
Now you have the cashflow from the business to support the RE. Then you can optimize operations exactly like you were saying to be more cashflow heavy - sell a couple, take some of the profits and invest in safer investments.