For first 2 points:
1: In single Job, add 2 steps for 2 programs and schedule that. It will cover condition1 and 2.
2. Create 2 separate jobs. First schedule as per normal ime. Second one schedule, In start condition, you need give AFTER JOB and give name of Job 1 and check "Status dependent"
For third point, If it is custom program, Then Update standard parameter table with equired condition at then end of program. Means you can update last run date as per condition and check the same at initial of program.
