You should be good with noninsulated boots and good wool socks.Waterproof comes in handy.There's always grass with dew,sometimes melting snow patches and most good bear country has some streams to cross.
If you find isolated water holes like elk wallows,in otherwise dry country,they can be good.You will be close to the rut and those are meeting places.After a rain,they will go dead for a couple days.
Don't discount the middle of the day.Mornings and evenings may be best but they will move any time of day,especially in the timber and at water holes,maybe not as much on the wide open slopes that are good for glassing.
If you find a sow with yearling cubs,she should be close to kicking them off and coming in heat.There should be boars cruising,even if she isn't ready.
On prominent trails,look for rub trees.Here,cedars are commonly used but you may not have them.These trees will usually show claw marks and some bite marks at head height.The bark will have hair in it.Any size tree may be used and trees leaning in to the trail are a plus.Multiple bears,male and females will hit them.Once you see one,you will start recognizing more.They start marking right out of hibernation and it gets more frequent toward the rut.
I haven't tried all the different boots but I have a pair of Asolo's that have been real good and have lasted a long time.They give good support,are comfortable and shed water.I honestly can't remember if they are 520's or 535's but don't think you could go wrong with either.Schnee's uninsulated packs are great for traction and wet condition but I need a little more support in rough country.I still like them for Spring bear hunting,where I'm not doing a ton of hiking in rocky,mountainous country.
A shot bear should stay good overnight.I like light for tracking,especially in grizzly country.
Whipcord trousers should be very good.When it starts getting closer to 70 degrees,I'm starting to wish I had cotton blend trousers but they are still tolerable.
I would also recommend a pair of collapsible trekking poles.The ones I use are Leki.