Hello everyone, and Happy Easter to everyone who celebrates it!

My apologies for not being much here lately. Things have been beyond hectic. I have good health news which I will post later tonight in the Off Topic.
I am also finally going home to Europe next week after not seeing my family for 5 years and am super excited! It will be a four week trip, two weeks home, than one week to Milan for a conference and finally back home for one more week. For Milan I need business casual clothing, for home trendy smart casual/casual. Both places are expected to have typical nice spring weather with some rain.

As you can imagine, the packing will be an absolute nightmare. I will need to check in two large suitcases and pay for the second one. While I own a typical three suitcase set ( a carry-on and a medium and large for checking in), I have ordered this super light large suitcase to use instead of the medium one:
http://www.ebags.com/product/i.....ion-285-pa
I have a also ordered a couple of those compression bags. Nevertheless, I will still have lots of issues packing. I need to pack the following categories:
1. A ridiculous numbers of clothing (and other) items as presents for various family members and cousins. This includes super bulky items like a down and leather man's jacket size XL and three pairs of large men's sneakers. This is by far the largest category and non-negotiable.
2. A bunch of sweets and food items for presents. Depending on final available space and weight of the suitcases, I may end up not packing much in this category at all.
3. A business casual capsule for a 6-day conference in Milan. Also non negotiable, and I will make a separate post in a day or two to figure it out.
4. A trendy smart casual capsule for home. The size of this will vary depending on the available space. Separate post will follow for this as well. Since I am staying home this does not need to be whole three weeks worthy of clothing, more like 7-10 days, as I can do laundry etc.
5. I have an excellent and affordable seamstress at home, so am hoping to bring a bunch of items (5-10) that need alterations, which would be quite pricey here. Not sure how essential this is. A separate post will follow for this too.
6. Similarly, I would like to buy and bring some nice natural fabrics for her to sew me some high-neck summer tops. Again not sure on how essential this is either.

Major problem area will be shoes for me. I do not have space for 5 pairs, yet I will need lots of diversity. Outerwear wise, I will need one trench and one leather jacket, one of which will be worn on the plane, so that is fine.

Areas where I can save space are the following:
1. Will not be bringing any lounging/stay at home casual clothes. I will buy those cheaply at home.
2. Toiletries/cosmetics: while I will bring small/travel sizes of my favorites, I will buy large bottles of shampoo/conditioner/lotion etc. on the spot.

Obviously I also need to bring some smaller things like meds, electronics (including my laptop)etc.

Do you ladies have any general advice before I start pondering all the separate categories? This may very well be the most complicated packing I ever had to do, and I only have a week to figure it out...