Do you plan to use the equity from this sale right away—or would it sit idle? (If it sits, are you better off collecting passive income in the meantime?)
If you keep the property, are you willing to adjust rent to meet market rates? (Current market rent for similar 2-bed, 2-bath homes in Dover averages $2,857/month—nearly $34,000/year gross. If you’re charging $2,000 or less, that’s over $10,000/year in missed income.)
Do you qualify for the capital gains exclusion—or will this be a taxable event? (If you’ve lived in the property for at least 2 of the last 5 years, you may qualify. If not, gains in the $65K–$75K range could trigger a tax bill of $10K–$15K.)
What is the cost of keeping this property when you factor in taxes, maintenance, and emotional bandwidth? (Annual property tax alone is $8,640—and that’s before you account for seasonal repairs, turnover costs, or vacancy.)
Do you want to manage this rental—or simply own it? If you decide to keep the home, you’ve got two paths:
Self-manage: You’ll handle tenant relations, rent collection, repairs, emergency calls, snow removal, and lease compliance. Ask yourself: Do I want to get a phone call at 9PM if a pipe bursts?
Delegate management: You can contract me as your property manager—someone who already knows the home, the market, and your goals—or work with a third-party firm like Universal Property Management, who specialize in full-service, no-fuss rental operations.
With me, you get:
Tenant screening & placement
Rent collection & accounting
Maintenance coordination
Lease compliance & legal support
Annual rent reviews + market re-analysis
With Universal, you get:
A larger, hands-off property management team
Corporate-level processes and systems
A more traditional, detached structure (sometimes preferred for emotional distance or long-term rentals)
👉 Bottom line: You don’t have to choose between selling and stress. You can hold the asset and still make it passive.
❤️ Personal & Emotional
Is your daughter planning to stay long-term? And if so, would that be as a tenant or a co-owner?
Do you feel peace of mind knowing the condo is yours—or is it starting to feel like a burden?
If something unexpected happened—health, relocation, opportunity—would keeping this home make that harder or easier?
Do you still feel emotionally connected to Dover, or has that chapter started to close?
What would make you feel proud, empowered, or relieved six months from now? (That’s your compass. Let the numbers serve that—not the other way around.)