Let me try and sort thru a few issues. Intercepting a radial is such a basic IFR maneuver that all IFR pilots are required to use. It is so basic, that it is part of the currency requirements to act as PIC on an IFR flightplan.
From 61.57 (c)(1):
(iii) Intercepting and tracking courses through the use of navigational electronic systems.
Use of a DP or ODP is a way, but not the only way of a part 91 aircraft to depart an airport runway and enter the IFR enroute structure. A DP is never part of an IFR clearance although an ODP may be. One has no way of filing a DP in a flightplan route, yet they are used all of the time.
There is no prohibition on using DR legs to intercept and join a VOR radial and all that is required is a VOR receiver to be properly equipped to accomplish this. The climb from the airport to the minimum altitude in the enroute structure is potentially without positive course guidance and the pilot is responsible for terrain clearance during the climb unless they are on radar vectors. Once reaching the centerline of an airway and at the MEA, the pilot is assured of terrain clearance, VOR reception, and communication unless otherwise noted by a MRA.
The primary issue is that one can't file a route in the system that uses an airway unless it starts at a fix or VOR, so a route that requires an airway to be intercepted or a radial to be intercepted is not able to be filed. However, clearances that specify intercepting a radial can be issued by ATC and /U aircraft can fly them without any difficulty.
The closest route to the intended route that can be filed is to the first fix on the airway in the direction one intends to fly on the airway. Because, direct to this fix is a random route, it technically requires RNAV capability. This makes filing the route in the system conflict with the precise route the /U aircraft intends to fly. However, this doesn't mean that the pilot is automatically in violation of the 91.205 regulation which requires the aircraft to be equipped with "navigation equipment suitable for the route to be flown." This is because there is one step after the flightplan is filed, that is the reception and acceptance of the clearance. At the time the clearance is issued, the pilot can request to be cleared to intercept the airway and proceed to the fix as they are /U.
As a similar example, see the DP for South County Airport of Santa Clara and read the DP. There is no way for a /U aircraft to file a flightplan and technically comply with the DP routing to the south on V485 as the first waypoint along the route GILRO would have to be used and in a similar way, the route as filed would imply an RNAV capability. However, I can assure you it is done all the time without any difficulty whatsoever.
DEPARTURE PROCEDURE: Rwy 14, all aircraft, climb to 2100 on heading 141°. Aircraft departing northwest on V485, climbing left turn heading 284° to intercept SJC R-121 (V485) to SJC VOR/DME and proceed on course; aircraft departing southeast on V485, climb on SJC R-121 and proceed on course. For climb in visual conditions: cross San Martin airport northwestbound at or above 1900, then climb on SJC R-121 to SJC VOR/DME. When executing VCOA, notify ATC prior to departure. Rwy 32, all aircraft, climb to 1600 on heading 321°. Aircraft departing northwest on V485, climbing left turn heading 270° to intercept SJC R-121 (V485) to SJC VOR/DME and proceed on course; aircraft departing southeast on V485, climbing left turn heading 120° to intercept SJC R-121 (V485) southeast bound to GILRO INT and proceed on course. For climb in visual conditions cross San Martin airport northwestbound at or above 1900, then climb on SJC R-121 to SJC VOR/DME. When executing VCOA, notify ATC prior to departure.