You may be in a check, but the ATC will not.
If you come via SOFIA and they offer ILS 2? DAL base turn procedure, take it and do not make any holding. Just anticipate the turn to be established in the outbound nicely. Don descend till established, which is no problem because you have plenty of miles to achieve final altitude. You should be at minimum clean or with first flap slat configuration before reachin DAL, though. That is what they expect.
If you are directed via DAM ATC should tell you if you are to make a hold. If they don't mention, ask them. Don't have doubts during a check. Request doing it if you are high, which often occurs.
Sometimes there is a lot of traffic in OSDI (a few traffics is a lot for them because it is conventional control, although they can see you with a radar). May be you have to hold over DAM to allow for a departure.
In OSDI you never know, with the ATC.
break a leg!