Strategies
Building a small portfolio over ten years
What a realistic accumulation actually looks like, with the pace and the constraints stated rather than assumed away.
Alan Whitfield
34 articles by Whitfield
Strategies
Wholesaling, and what it actually involves
Contracting a property and assigning the contract for a fee is a real business with a marketing engine at its centre and a growing set of legal constraints.
Financing
Paying off the mortgage early, or not
A question with a clear mathematical answer and a legitimate non-mathematical one, and the two frequently disagree.
Underwriting
The assumptions that break deals, ranked
A summary of where underwriting actually goes wrong, in rough order of how much money each error costs.
Strategies
Buying land, and why it is harder than it looks
No tenants, no maintenance, no repairs — and no income, no depreciation and financing that barely exists.
Financing
Assumable loans and why they matter again
A low-rate mortgage attached to a property has become a significant asset in its own right, and a minority of loans allow it to transfer.
Financing
The HELOC and other ways to use existing equity
Equity in a property you already own is the most accessible capital most investors have, and the most dangerous to deploy carelessly.
Underwriting
Reading operating statements a seller prepared
The document is real. Whether it describes the property you will own is a separate question.
Underwriting
The offer: contingencies, timelines and leverage
Price is one term among many, and the others frequently determine whether you win the property and whether you regret it.
Strategies
Flipping: a business, not an investment
Buying to renovate and resell generates income rather than assets, and the tax treatment and risk profile follow from that distinction.
Tax & Structure
Estate planning for property owners
Real estate transfers badly without planning, and the costs fall on people who did not choose to be in the business.
Financing
What lenders look at besides the property
The property is one of four things being underwritten, and the other three are about you.
Financing
Interest rate caps, swaps and floating-rate debt
Floating-rate borrowing transfers rate risk to you, and the instruments that hedge it have costs and expiry dates that recently caught a great many people out.
Underwriting
Underwriting a value-add plan without fooling yourself
The gap between a renovation budget and a renovation outcome is the most reliably underestimated number in the business.
Strategies
Buy and hold, and the case for boring
The least discussed strategy is also the one that has produced most of the wealth in this asset class, largely by not doing very much.
Tax & Structure
Partnerships: the agreement is the whole thing
Most real estate partnerships fail on governance rather than on the property, and the failures are predictable enough to be drafted around.
Financing
Bridge loans and the exit that has to exist
Short-term debt solves a timing problem and creates a deadline, and the deadline does not care whether your plan worked.
Financing
Working with a mortgage broker versus going direct
Different channels reach different lenders, and the investor who only ever calls their own bank is seeing a fraction of the market.
Underwriting
Valuing small multifamily when the comps do not exist
Two to four units sits awkwardly between residential comparables and income capitalization, and which method applies determines the price.
Strategies
Syndications: what a limited partner is actually buying
Passive real estate through a sponsor, where the returns depend more on the sponsor than on the property, and the illiquidity is total.
Financing
Personal guarantees and what recourse really means
Non-recourse does not mean no personal exposure, and the carve-outs are where the exposure lives.
Financing
Seller financing, from both sides of the table
A genuine tool with real advantages for both parties, surrounded by more nonsense than almost any other topic in the business.
Underwriting
Stress testing a deal before you sign
The base case tells you what the deal does if you are right. The stress case tells you what happens when you are not, which is the more common condition.
Underwriting
Internal rate of return, and what it hides
The metric that accounts for timing is also the one most easily manipulated by changing assumptions nobody checks.
Tax & Structure
Should you hold property in an LLC?
The most common structural question in small-scale investing, with an answer that depends on facts people rarely state.
Financing
When refinancing makes sense, and when it is just fees
Refinancing has three legitimate purposes and one common bad reason, and telling them apart requires only arithmetic.
Financing
Conventional, portfolio, DSCR and hard money
Four broad categories of investor lending, each with a purpose, and the cost of using the wrong one is measured in points.
Underwriting
Building a rent roll you can trust
The document the seller hands you is a summary of claims. Verifying it is the most productive hour in any acquisition.
Strategies
The BRRRR method, and where it breaks
Buy, rehab, rent, refinance, repeat is a real strategy with real mechanics, and the versions taught online skip the parts that fail.
Financing
How much should you put down?
The maximum leverage available is rarely the right amount, and the arithmetic that argues otherwise assumes nothing goes wrong.
Financing
Fixed, adjustable and everything in between
Rate structure matters more to outcomes than the headline rate, and the difference shows up years after closing.
Underwriting
DSCR: the number your lender cares about most
Debt service coverage ratio decides whether a loan gets made, at what size, and how much room you have before the deal is in trouble.
Underwriting
Cash-on-cash return, and why leverage flatters it
The metric that tells you what your money earns also makes the riskiest deals look the best, which is worth understanding before you use it.
Underwriting
Cap rate is not a return, and treating it as one costs money
The most quoted number in the business is a pricing convention, not a measure of what you will earn.