@Renee PohleStarting with a primary residence in Boston offers long-term stability, house hacking potential, and equity building, but may have high upfront costs and limited cash flow.

Bet you know who that is don't ya Carlos? 

In my area the supply is always going to be limited.

It's clear from your post, and the limited information you put in there, that you are out ahead of your skis here.

Keep in mind the area surround Temple University has a zoning overlay that limits density beyond what the same zoning classifications allow in other areas of Philadelphia.

Using a Self-Directed IRA (SDIRA) allows pre-tax dollars to grow tax-deferred in real estate, but limits flexibility due to IRS rules and potential UBIT on leveraged properties.Investing through a Roth IRA offers tax-free growth and no RMDs, but funding limits and restrictions apply.

I know certain areas where I live are limiting those types of permits, etc.

Maxmimum loan amounts for FHA are the same across the nation for the most part except for the high cost areas of the west, east coast, or specialty markets like Aspen, CO Los angeles, New York, NY, and others as they have higher limits for 1-4 unit FHA loans.

I bet there are some ways you could proactively plan so the problem almost resolves itself. 

It works anywhere within Seattle city limits.