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Boeing, although it produced many larger narrowbodies, never designed its own regional jet; the only regional jet it ever produced was the DC-9 (from 1997 through 2006, in the DC-9-80 and DC-9-90 series), a (McDonnell) Douglas aircraft which Boeing inherited from Long Beach through a corporate merger.
Why didn't Boeing design and build its own regional jet earlier, to compete with the DC-9?
Boeing did have a small regional jet called the Boeing 727. This plane was designed to operate at smaller airports, with independence from ground facilities as a selling feature. The best example is that the 727 had built-in stairs in the rear underbelly of the aircraft. This could be opened in flight until some hijacker known as DB Cooper jumped out to make his escape.
The 727-100C could have a combination of 54 passengers and four cargo pallets of freight or up to 94 passengers in a mixed class with no freight.
Until it ended production at 1,832 aircraft, the 727 was the most popular passenger jet ever sold. Since that time, the most popular plane ever sold was the Boeing 737, which could have as few as 85 passengers with the 737-100.
Boeing met a definite need for airlines since it sold so many aircraft. A better question might be what could McDonnell-Douglas have done to meet airline needs and still be a viable competitor.
Two Class Seating Arrangement:
Well it did have one in the form of the ‘slugs’ - the earlier 737 classic aircraft. They sold outrageously well along with the 727s to fill regional or national routes.
And let’s not forget the airline business was considerably different than it is today in the form of structure and operations so what we consider a ‘regional’ aircraft is very different to what it was back then.
It really wasn’t until the 1990s with deregulation in full force and changes to the labor structure of the airlines going over to the ‘hub and spoke’ approach to travel, which facilitated the rise of the regional carriers and the intro of the fast and efficient 50-60 passenger regional jets. I suspect back in the ‘golden age’ of air travel pre deregulation and oil embargo, when 747s were a status symbol and iconic of the glamour of jet setting, there just would not have been a market, an interest, or both, in a large enough setting to justify investing in a jet that small.
Boeing is heavily involved in design and marketing this beauty, the Sukhoi Superjet 100. 78 or 98 seats, with talk of a stretch or two to 120 and 140. Russian built, with largely Western engines, subsystems and avionics. It was poised to do quite well in the RJ market until Euromaidan/Crimea/Donbass threw a big monkey wrench in the political situation. The aircraft is also having the teething pains one expects from a blank-sheet design, and had one all-souls loss entirely not the aircraft or engines' fault. Still, the Superjet soldiers on, and it is closing some sales, with 300 orders on the books. Pretty spectacular for a Russian aircraft, and that's because of Boeing.
The famous and popular -800, -900, -8 and -9 stretch so far beyond original design concepts that they actually have tail-strike risks.
Boeing inherited the DC-9 as part of the McDonnell-Douglas merger (which was mostly about military aircraft). This could have been their RJ, but they failed to continue developing it. though, so we don't have a "717 Max 4" or anything (couple of GE Passports, wouldn't that be nice!)
Boeing also passed on opportunities to gain an RJ via acqusition of Fokker or Canadair. The Sukhoi toe-dip is as close as they've gotten.
The 737 was basically created to be Boeing's regional jet, but ended up growing into something larger to meet customer demand.
The DC-9 was introduced in 1965 and had variants seating from 90 to 135 in a single class. The 727-100 was introduced around the same time and already covered the upper end of this range. The 727-200 was even larger, almost comparable to a modern 737, so it wasn't really a "regional jet" as we would describe it today, and didn't compete directly with the DC-9. Boeing was looking for something to supplement the larger 727 and better cover lower capacities.
The 737-100 was introduced in 1968. It was designed to be low enough to the ground to allow built-in air stairs and for ground crew to be able to load/unload baggage without equipment. The capacity of 103-118 in a single class placed it right in the middle of the DC-9 market, but the DC-9 and other competition already had a head start. Only 30 of these were built, mostly for Lufthansa. The 737-200 was introduced to meet customer demand for something larger, seating 115 to 130 in a single class. This covers the upper range of the DC-9 family, and over 1,000 of these were built, surpassing the DC-9. These variants were even powered by some of the same variants of the Pratt & Whitney JT8D that the DC-9 used. It carried slightly fewer passengers than a 727-100 but was much lighter and with only 2 engines would have been cheaper to operate. With a gravel kit it could operate even on unpaved runways, and a few examples are still flying for this reason.
The 737-500 was the Classic version that was introduced in 1987 to replace the 737-200, and almost 400 of these were built. The 737-600 was the Next Generation version to replace the 737-500. The 737 had grown to optimally carry more passengers, and only 69 were built. The last 737-600 was built in 2006, with some orders being converted to the slightly larger 737-700. The smallest 737 MAX is the -7, which is slightly larger than the -700, and has not sold very well.
While the 737 NG was ramping up, Boeing did produce what began as the McDonnell Douglas MD-95 under the Boeing 717 name, but production ended amid slow sales. When the market for this size of plane picked up again, Boeing decided not to compete with companies such as Bombardier and Embraer in the regional jet market, as that would probably require a completely new design.
Other answers have noted the history of both the 727 and 737, which started as small regional jets, but grew due to demands from established customers. Regional jets, by contrast, tend to be flown by smaller, regional airlines that transitioned from turboprops (such as the the Bombardier Dash 8) and consequently went to the same manufacturer when they wanted to transition to a regional jet.
To directly answer the question, Boeing apparently did not develop their own regional jet in-house because:
Instead, when it was finally apparent to them that they needed a regional jet, they elected to make a buy-versus-build decision and entered into a majority stock purchase of Embraer (after the Brazilian government made it clear that an outright acquisition was out of the question). This keeps the development isolated, hence addressing the first concern, and limits their exposure, hence addressing the second concern.
