Start Here: Real Estate

The real estate series in reading order: from rent-or-buy to cap rates.

Real estate is the topic I have written about most on this blog. If you are new to the series, this is the reading order I would suggest. It builds each concept on the previous one, starting with whether owning makes sense at all and ending with the metrics I use to evaluate actual deals.

The Foundations

  1. The Upside of Homeownership: the case for why owning is worth considering in the first place.
  2. Real Estate vs. the S&P 500: how property returns compare against simply buying the index.
  3. The Price-to-Rent Ratio: a single number that helps frame the rent-or-buy decision.
  4. Boston's Neighborhoods: where the numbers still look reasonable in my own market.

The Playbook

  1. Why I'm Considering an FHA Loan: the low-down-payment path into multifamily.
  2. House-Hacking: living in one unit while the others help pay the mortgage.

The Math

  1. Cash-on-Cash Return: the first metric I evaluate deals with.
  2. Cap Rates: what the market's favorite shorthand actually tells you about risk and return.

More is coming as my own property search continues. If you only have time for two, the S&P comparison and cash-on-cash cover the most ground.