Your next career move—whether staying at Dover High, pursuing a master’s, or relocating for a PhD—will have a direct impact on your real estate strategy. Here are some key questions to help you think through your options:
1. Teaching & Higher Education—What’s the Long-Term Plan?
Do you see yourself staying in teaching long-term, or is this a stepping stone to something else?
If you stay at Dover High, is having them pay for your master’s worth it? Does it lock you into a commitment you’re comfortable with?
If you pursue a PhD, would you want to own property before relocating or wait until you settle into a permanent location?
If you plan to keep teaching, a PhD could open doors to teaching at the college level—but tenure-track positions are getting harder to secure, and adjunct roles don’t always pay well. Would that be a worthwhile trade-off?
High schools typically don’t favor hiring PhDs because they have to pay them more upfront. Does that make a master’s the better financial move if you stay in secondary education?
2. How Does Real Estate Fit Into Your Future?
Do you want to buy a home sooner and keep it as an investment property later?
Would you prefer renting longer and buying only when your career is more settled?
If you relocate for a PhD, would you still want to own property in NH, or would it make more sense to buy after you finish and know where you’re going?
Are you open to house hacking (buying a multi-unit property and renting part of it)?
3. Financial Strategy—What’s the Smartest Move?
If Dover High covers your master’s, does that free up savings for a down payment?
If you go for a PhD, would assistantships cover tuition + living costs, or would you be taking on debt?
Are there state or federal first-time homebuyer programs that align with your financial situation?
Would a side income from rental properties help offset grad school costs or give you long-term financial security?
You seemed surprised by my average commissions—would you ever consider getting a real estate license as a part-time income stream?
You could show houses on weekends without doing the full hustle.
Or you could sell real estate during summers, keeping flexibility while adding income.
Keller Williams offers a 100% reimbursable training program, which could be a no-risk way to explore it.
4. How Much Flexibility Do You Want?
If you’re still deciding between paths, does buying now limit your options later?
Or would owning property sooner give you more security and leverage down the road?
What’s the right balance between stability and opportunity for you?
What’s the opportunity cost of each decision?
What’s the opportunity cost of not purchasing property now?
What’s the opportunity cost of not pursuing a PhD now?
What’s the opportunity cost of not having Dover High cover your master’s in education?