Since you wanted to do a visa run anyway, you could have 30 days in Sumatra, fly out to Malaysia, then fly to Java and extend this time.
I wouldn't do Medan-Jakarta in anything less than 4 weeks personally. More time would be better. Sumatra's huge, the roads are bad, and there is a ton to see.
I think Laszlo's plan is a good one.
I recently got a VOA in Medan -- no problems, no outward flight required. Just wanted to know where I would be staying in Medan (normal procedure).
Now I am extending -- previously I had applied on Day 1 and (midday) paid at the immigration office and received the extension on Day 2. Now this seems to have changed.
This time -- Day 1 (morning) filled in the form to apply for the extension and was given a paper to take to a bank and bring back the next day (morning). Day 2 show the receipt from the bank then get my photo and fingerprints taken. I also answered a few questions (I think they were friendly) but they pointed out that my ticket out was a day late and could leave on time or pay a 300,000 IDR fine. Sounded good but (surprise) I had to come back on Day 3 to get my passport back -- so I am sitting in Medan for an extra two days.
By the way -- the counter for foreigners is now conveniently located on the ground floor (first floor for North Americans) on the left of the information desk. (The whole ground floor area has been redesigned with space, previously in the grounds, now being used as a waiting area,)
I have posted here on TT my previous experiences of 2 years ago -- so this is an update.
Paul
When I tried to take a Jetstar flight from SYD to DPS, the ground staff insisted that I had to have a ticket out of Indonesia within 60 days before I could board.
Similarly, when I tried to take a AA flight from KUL to DPS, the ground staff insisted that I had to have a ticket out of Indonesia before I could board.

FYI - I got a 60 day visa in London before I arrive and it was really easy. Took about 1-2 weeks, I went to the embassy twice in St James Park and only had a flight in and out arranged. It cost £45 for single entry. If you don't live in London you send them a passport and the docs I think. My friend got stuck in one place extending her visa in Indonesia and it sounded like it would be more of an organisational mess! She didn't recommend it.
I have gotten a VOA on most of my trips in recently and the extension process in Medan has always gone smoothly. Especially as there is a copying service close by. I have also gotten a visa in advance in BKK a few times. There you put your application in on the morning of Day1 and got your visa back on the afternoon of Day2. As I stay on the outskirts of BKK and I travel by bus this takes 2 full days. Doing the same in Sydney used to be: Day1 apply, Day5 get the visa back. Parking was very hard and public transport difficult. (It is quite a few years since I have gotten a visa in Sydney so my information might be out of date.)
Paul
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