Hello Mr OC Benz!
As I see you need an information about travelling to Blagoevgrad. From Macedonia to Blagoevgrad you can travel by several different routes:
Skopie - Sofia: 08:30 / 12:40 arrive in Sofia / (Kaleia company) then
Sofia - Blagoevgrad: 13:20, 14:10, 15:00, 15:30, 16:15 .... last 19:00 (Skaptopara-5 company, sector 26 / Central busstaion Sofia - tickets buy from driver - 10.00 BGN). Other option is to make a transfer in Kyustendil, see Kyustendil bus staion schedule
. Other options from Skopje: 15:00, 17:30, 00:00
3rd option: Strumica - Sofia: 03:00 from Strumica, 06:30 in Blagoevgrad (Transit Express BG / Strumica Express)
4th option: Delcevo - Blagoevgrad: 15:00 and 06:00.
3rd and 4th option are good if you could rech Delcevo or Strumica. However i think Skopie - Sofia - Blagoevgrad will be the best option for you.
Also if you are interested, check bus company ALPAR Turizm / Domino line Skopje - they travel from Skopje to Istanbul but also there is direct bus from Istanbul to Blagoevgrad so i think they make a transfer in Sofia. Ask them if you could travel from Skopje to Blagoevgrad directly (that trip will probably be during the night because the bus arrives from Istanbul (20:30 leaves) in Blagoevgrad at 06:30-07:00 on the next morning).
From Blagoevgrad to Plovdiv there are buses at 06:20 (passes through Belitsa, Yakoruda, Velingrad - a picturesque route) and arrives in Plovdiv around 11:50. Other option is 06:30 (passes through Dupnitsa, Samokov, Pazardjik. Also there is other bus at 14:00 (passes through Borovetz ski-resort, Medilin SD company) and 17:30 (bus to Istanbul - company Alpar/Matpu-96).