Co-hosting
Service
CONSULTING
SERVICES
Finance-backed short-term rental investment consulting built by a former corporate finance leader and active STR operator. I help serious investors underwrite deals with discipline, launch with professional systems, and scale with clarity.
Buy Smarter STRs. Launch Cleaner. Scale Faster.
Finance-backed short-term rental investment consulting built by a former corporate finance leader and active STR operator. I help serious investors underwrite deals with discipline, launch with professional systems, and scale with clarity.
Co-Owner,
Lush Living Designs
Active STR Operator
Former Assistant Vice President, Capital Management
10+ Years in Financial Analysis & Risk Management
Founder,
Cozy Quarters Management
Built on Enterprise Finance.
Proven in Real-World STR Operations.
Today, she applies that same rigor to short-term rental investing.
Nichole is:
Nichole is:
- Founder of a boutique STR management firm operating in North Carolina Co-owner of a nationwide short-term rental design firm
- An active STR portfolio operator
- A finance-backed advisor helping investors underwrite, launch, and scale profitable STR assets
Nichole DiPippo brings over a decade of experience in corporate finance, capital management, and enterprise risk analysis to the short-term rental industry.
Before founding her STR companies, she held senior finance leadership roles within publicly traded and enterprise-level organizations, where she was responsible for:
- Capital allocation strategy
- Enterprise risk management
- Portfolio-level financial oversight
- Multi-million-dollar project financial modeling
- Revenue forecasting & margin optimization
- Financial review of $500M+ in business proposals
Her background includes leading financial analysis across complex, multi-department organizations — delivering disciplined modeling, risk mitigation strategies, and executive-level reporting.
Nichole DiPippo brings over a decade of experience in corporate finance, capital management, and enterprise risk analysis to the short-term rental industry.
Before founding her STR companies, she held senior finance leadership roles within publicly traded and enterprise-level organizations, where she was responsible for:
- Capital allocation strategy
- Enterprise risk management
- Portfolio-level financial oversight
- Multi-million-dollar project financial modeling
- Revenue forecasting & margin optimization
- Financial review of $500M+ in business proposals
Today, she applies that same rigor to short-term rental investing.
Nichole is:
Nichole is:
- Founder of a boutique STR management firm operating in North Carolina Co-owner of a nationwide short-term rental design firm
- An active STR portfolio operator
- A finance-backed advisor helping investors underwrite, launch, and scale profitable STR assets
Her background includes leading financial analysis across complex, multi-department organizations — delivering disciplined modeling, risk mitigation strategies, and executive-level reporting.
STR FREEDOM ADVISORY
service offerings
Nichole's approach combines corporate-level financial discipline with real-world operating experience — giving investors clarity beyond surface-level revenue estimates.
Scroll through to see our Five Tiers of service offerings - including an exciting new offering that's coming soon.
Scroll through to see our Five Tiers of service offerings - including an exciting new offering that's coming soon.
Nichole's approach combines corporate-level financial discipline with real-world operating experience — giving investors clarity beyond surface-level revenue estimates.
Scroll through to see our Five Tiers of service offerings - including an exciting new offering that's coming soon.
Scroll through to see our Five Tiers of service offerings - including an exciting new offering that's coming soon.
investment: $495
Strategy Intensive
tier 1
Includes:
- 60-minute private Zoom session
- Evaluation of one property or deal
- Revenue reality check
- Regulatory red flags overview
- Expense stress-test discussion
- 3–5 tactical next steps
- Call recording
Includes:
- 60-minute private Zoom session
- Evaluation of one property or deal
- Revenue reality check
- Regulatory red flags overview
- Expense stress-test discussion
- 3–5 tactical next steps
- Call recording
investment: $2750 per property
STR Investment Analysis Package
tier 2
Includes:
Optional Add-On:
- Market demand validation
- Conservative / Moderate / Aggressive revenue projections
- Full expense pro forma
- Cash-on-cash return modeling
- Cap rate estimate • Sensitivity analysis (occupancy & ADR shifts)
- Regulatory review summary • Risk profile score
- 45-minute review call • Branded investor report PDF
Optional Add-On:
- 12-month pricing strategy framework ($500)
Includes:
Optional Add-On:
- Market demand validation
- Conservative / Moderate / Aggressive revenue projections
- Full expense pro forma
- Cash-on-cash return modeling
- Cap rate estimate • Sensitivity analysis (occupancy & ADR shifts)
- Regulatory review summary • Risk profile score
- 45-minute review call • Branded investor report PDF
Optional Add-On:
- 12-month pricing strategy framework ($500)
FLAGSHIP OFFER
investment: $6500
For investors planning to self-manage or launch strategically.
tier 3
Includes:
Optional Add-On:
- Everything in Investment Analysis
- Design-for-ROI strategy outline
- Listing positioning strategy • Pricing structure framework
- Technology stack recommendations (PMS, automation, cleaning ops)
- SOP architecture template
- Vendor checklist
- Two private strategy calls
Optional Add-On:
- 30-Day Pricing Implementation Support ($2000)
Launch Blueprint
Includes:
Optional Add-On:
- Everything in Investment Analysis
- Design-for-ROI strategy outline
- Listing positioning strategy • Pricing structure framework
- Technology stack recommendations (PMS, automation, cleaning ops)
- SOP architecture template
- Vendor checklist
- Two private strategy calls
Optional Add-On:
- 30-Day Pricing Implementation Support ($2000)
investment: $12,000 (90-day engagement)
For investors scaling 3+ properties.
tier 4
Includes:
- Portfolio-level financial modeling
- Capital allocation discussion (non-legal advisory)
- Market diversification strategy
- Risk compression planning
- 90-day scaling roadmap
- Three private 90-minute sessions
- Direct Slack access during engagement
Portfolio Scale Advisory
Includes:
- Portfolio-level financial modeling
- Capital allocation discussion (non-legal advisory)
- Market diversification strategy
- Risk compression planning
- 90-day scaling roadmap
- Three private 90-minute sessions
- Direct Slack access during engagement
investment: $14,000/year or $1350/month
tier 5
STR Freedom Mastermind
Application-only, limited seats.
- Private Slack community
- Guest experts (CPA, attorney, lender)
- Annual in-person retreat (travel separate)
Includes:
- Monthly live deal reviews
- Financial modeling workshops
- Quarterly scale intensives
COMING SOON
- Private Slack community
- Guest experts (CPA, attorney, lender)
- Annual in-person retreat (travel separate)
Includes:
- Monthly live deal reviews
- Financial modeling workshops
- Quarterly scale intensives
STR FREEDOM ADVISORY
service offerings
investment: $12,000 (90-day engagement)
For investors scaling 3+ properties.
tier 4
Includes:
- Portfolio-level financial modeling
- Capital allocation discussion (non-legal advisory)
- Market diversification strategy
- Risk compression planning
- 90-day scaling roadmap
- Three private 90-minute sessions
- Direct Slack access during engagement
Portfolio Scale Advisory
investment: $495
Strategy Intensive
tier 1
Includes:
- 60-minute private Zoom session
- Evaluation of one property or deal
- Revenue reality check
- Regulatory red flags overview
- Expense stress-test discussion
- 3–5 tactical next steps
- Call recording
investment: $2750 per property
STR Investment Analysis Package
tier 2
Includes:
Optional Add-On:
- Market demand validation
- Conservative / Moderate / Aggressive revenue projections
- Full expense pro forma
- Cash-on-cash return modeling
- Cap rate estimate • Sensitivity analysis (occupancy & ADR shifts)
- Regulatory review summary • Risk profile score
- 45-minute review call • Branded investor report PDF
Optional Add-On:
- 12-month pricing strategy framework ($500)
investment: $6500
For investors planning to self-manage or launch strategically.
tier 3
Includes:
Optional Add-On:
- Everything in Investment Analysis
- Design-for-ROI strategy outline
- Listing positioning strategy • Pricing structure framework
- Technology stack recommendations (PMS, automation, cleaning ops)
- SOP architecture template
- Vendor checklist
- Two private strategy calls
Optional Add-On:
- 30-Day Pricing Implementation Support ($2000)
Launch Blueprint
investment: $14,000/year or $1350/month
tier 5
STR Freedom Mastermind
Application-only, limited seats.
Includes:
- Monthly live deal reviews
- Financial modeling workshops
- Quarterly scale intensives
- Private Slack community
- Guest experts (CPA, attorney, lender)
- Annual in-person retreat (travel separate)
Includes:
Optional Add-On:
- Market demand validation
- Conservative / Moderate / Aggressive revenue projections
- Full expense pro forma
- Cash-on-cash return modeling
- Cap rate estimate • Sensitivity analysis (occupancy & ADR shifts)
- Regulatory review summary • Risk profile score
- 45-minute review call • Branded investor report PDF
Optional Add-On:
- 12-month pricing strategy framework ($500)
