Investing
Check the investment before you make an offer.
Send me the deal you are considering. We will check the rent assumptions, ownership costs, and whether the property can support your plan.
Where To Start
Start with the deal you’re considering
Try the rental calculators, review past purchases, or ask me about a property.
Fit Check
Which rental strategy are you considering?
A long-term rental, apartment building, and room-rental house need different assumptions. We’ll check the ones that apply to your property.
Best Fit
Buy-hold, house-hack, and value-add investors
Best for investors screening Tampa Bay submarkets, rental fit, renovation tolerance, and exit flexibility before falling in love with a listing.
Still comparing
The projected return looks good. What could change it?
Bring the spreadsheet. We can check the assumptions against rent evidence, insurance quotes, property condition, and the rules for the use you have in mind.
Bring Into The Call
Strategy, budget, and hold assumptions
The strongest starting details are target strategy, budget range, financing plan, renovation appetite, rent assumptions, and which counties you are already considering.
Approach
What could change the return?
How you plan to rent it
A yearly lease, short-term stay and room rental have different costs and restrictions. We check the plan against the address before relying on projected income.
What it costs to own
Use insurance quotes, taxes after purchase, association fees and repair estimates. The current owner’s expenses may not be yours.
What happens if it falls short
Lower rent, longer vacancy and a major repair can change the decision. We can test those scenarios and consider what selling would involve.
Underwriting the property
Start with the income you can support
Projected rent is a starting assumption. I want to know what supports it and what happens when the property costs more than expected.
Read the full explanation
We compare rent evidence with insurance quotes, taxes after purchase, maintenance, vacancy, management, and financing. For a room-rental or short-term rental plan, we also need to check the address-specific rules and operating costs.
One-to-four-unit properties are commonly valued using comparable sales. Larger apartment buildings and commercial properties often rely more heavily on net operating income and market cap rates. Better operations can help, but higher expenses or changing cap rates can offset that gain.
We can compare cash flow and exit scenarios. Your CPA should confirm how depreciation, a sale, or a possible 1031 exchange would affect your own taxes.
Client Experience
What clients say about working with me
Dillon helped me through the whole process of purchasing my first home. He was knowledgeable and went above and beyond to answer any questions I had. Highly recommend to anyone looking for their first home or investment property.
Dillon was great throughout the whole sales transaction of one of my rental properties that was a little difficult, but he was very knowledgeable and found solutions to every problem that came up. He made a difficult transaction feel manageable and really took the stress out of the entire process. He is very knowledgeable at what he does and very professional. I will definitely be contacting him for other transactions in the future.
Decision Tools
Choose the estimate that matches your next question
Use one focused calculator to pressure-test the numbers, then bring the result into a conversation about the property and timing.
Calculator
PadSplit Feasibility Screener
Estimate room-rental cash flow and break-even occupancy before you look more closely at a Tampa Bay property.
Open this calculatorCalculator
Tampa Bay Rental Deal Analyzer
Check whether a Tampa Bay rental covers its financing, insurance, taxes, and reserves.
Open this calculatorNot sure which estimate applies? Start with the complete tool set and choose from one place.
Continue to the Calculator HubRecent Results
Closings connected to this service
See the property, recorded sale price, and closing date. Past sales are examples, not a prediction of your result.
Market Areas
Start with the county that matches the investment strategy
Use the county hubs to compare inventory age, insurance exposure, rentability, tenant profile, fees, and exit options before you underwrite a specific deal.
County Hub
Pasco Hub
Best for growth corridors, newer inventory, CDD-heavy areas, and address-based city coverage where the screening logic changes quickly.
County Hub
Hillsborough Hub
Best for Tampa neighborhoods, Riverview, Plant City, and mixed-strategy pockets where rentability and exit options vary block by block.
County Hub
Pinellas Hub
Best for urban and coastal inventory where insurance, flood, neighborhood feel, and use-case restrictions can kill a deal quickly.
Investor Plan
Have a property in mind?
Send the listing or address, your intended use, and how you expect to finance it. If you are still choosing a strategy, tell me your budget and how much work you want to take on.
I will tell you where I see an opportunity and where I would be cautious. Passing on a property is sometimes the right decision.
Tell Dillon what kind of deal you are evaluating
FAQ
Questions that usually come up before we talk
How do I know if a property is a good investment?
Start with evidence for the rent and estimates for the costs. Then test lower income, vacancy and repairs against your financing and cash reserves. I also look at the condition, permitted use and resale options. A projected return is only as reliable as those assumptions.
What is the difference between buying residential and multifamily or commercial property?
One-to-four-unit residential properties are commonly valued using comparable sales. Apartment buildings with five or more units and commercial properties often rely more on net operating income and market cap rates. Improving income can support a higher value, but financing, expenses, condition, and market changes still matter. Multifamily includes small properties too; five units is not the definition of every commercial property.
Should I sell my investment property now or hold onto it?
We can compare the income you keep after expenses with the proceeds from selling. Upcoming repairs, the work of managing it and what you would do with the money all matter. Your CPA should review the tax consequences and any possible 1031 exchange before you decide.
In Tampa, where can I get the best returns?
There isn’t one area or strategy with the best return for everyone. Room rentals can bring in more gross rent, but utilities, turnover, local rules and management costs can absorb the difference. We need to compare actual properties using your financing and the amount of work you want to take on.
What should I expect when working with you as my agent?
Send me the address or listing, intended use and financing plan. I’ll help check the rent and expense assumptions, identify questions for the inspector or local authority, and negotiate the purchase if you decide to proceed. I’ll also tell you when I think the numbers are too thin.
How should I evaluate a Tampa Bay investment property?
I recommend looking at three things: cash flow after all expenses, appreciation potential based on location and development trends, and the exit strategy if the market shifts.
I run comps and provide clients with property-specific ROI analysis so they can make decisions backed by numbers instead of guesswork.
What should investors screen first in Holiday?
Start with property-level condition, insurance pressure, and whether the neighborhood supports the strategy you want to run. Holiday can offer lower entry prices, but that only helps if the carrying costs, rent assumptions, and future resale story still make sense.
In other words, affordability is only the first screen. The real work is understanding what the cheaper price is buying you and what extra diligence it demands.
Is East Tampa more of a value-add market or an owner-occupant market?
It can be both, which is exactly why broad labels are not enough. Some pockets attract owner-occupants who want central Tampa access and character, while others make more sense as investor or value-add opportunities.
The right answer depends on the exact block, condition, layout, and what the long-term neighborhood story looks like around that property.