Owner-Led Property Management,
Led by Jason Caldwell

Proven Experience That Protects Your Investment

• 200+ units leased — real-world experience screening tenants, not theory

• 5+ years of hands-on property management — not a desk-only role

• Renovation & contractor experience — fewer surprises, smarter repairs

• Built for out-of-state owners — clear systems and proactive communication

• Local market knowledge from St. Pete to Spring Hill — pricing and tenants that actually fit the area

Meet Jason

I’m Jason Caldwell, a licensed Florida Realtor and full-time property manager.
I personally oversee every property I take on in Pinellas County, Hernando County, and South Tampa.

I started managing properties after dealing firsthand with poor property management on my own investments.I saw how quickly poor communication, lazy screening, and short-term thinking turn into late rent, constant turnover, and expensive mistakes for owners. I built this company to do the opposite of what costs most landlords:
no call centers, no runaround, and no decisions made without accountability. I’ve leased 200+ units locally and currently manage 40+ doors across the Tampa Bay area.

II stay directly involved in strategy and oversight, while support handles day-to-day coordination so issues get addressed quickly without losing control and nothing falls through the cracks.

Why Serious Owners Choose Jason Caldwell
to Manage Their Properties

Owners work with me because:

• They choose direct accountability, not layers of staff

• They choose fewer surprises, not constant explanations

• They choose problems handled once, not patched repeatedly

• They choose cash flow protected, not optimized on paper only

That’s the difference between basic management and ownership-level oversight.

Pinellas & Hernando County • Owner-led management