You'll get the feel for how often to strop - that 5/8 dovo blade is probably good for an entire shave. I have to strop mid-shave with a double hollow ground or if I haven't prepped and soaked my beard for long enough.

Definitely the first shave should be with NO stropping since it's pre-honed. Remember it well, that's your benchmark for that razor. You might be able to get through the first couple shaves without stropping.

When you do strop the first time, pull the leather real tight and give it about three strops and try a shave pass. If it feels about the same, keep going with your stropping. If it pulls a lot more or otherwise seems to have gotten duller then STOP and read more posts in the 'strops' forum.

It's remarkably easy to ruin an edge on a piece of leather if you do it wrong. When you get it right, it might not even take the 30 recommended passes. I do about 10-15 before a shave and it works.