You won't need insulation above the ceiling and below the old deck.Roofing over, the issue is to carry the load to the ground and trimming it off at the ends and at the soffits to look good.

color of house and trim?

We paint our properties a really light blue with white trim, it looks GREAT and it let's us stand out from all the "all white" properties out there.

You are obviously in a different market than mine, but here are my suggestions:- No siding on garage, just new paint- Leave the roof on garage as-is unless it is leaking or really old- Definitely remove the awnings- Upgrade to two full baths- Recoat or resurface the driveway rather than make it concrete unless concrete is standard for the area and for your comps- For missing plumbing, do whatever is expected for your area- Trim all bushes and also add some plants with colorful flowers- Do the basement wall if the basement will be living space or if required by code now, otherwise no- We never include washer and dryer here, but maybe it's different where you are- I'd suggest doing stainless steel or faux stainless appliances; it's not much more and they look a lot better- If you can get inexpensive, nice cabinets from a distributor, great, otherwise Lowe's has some nice looking cabinets for the price- We always do granite countertops at least, but that's normal here- If that basement floor sealant is inexpensive, I think it will make the basement feel a lot nicer

Because I had to go the the dump 6 times with trash, carpets, appliances and several trees that had to be trimmed.

Typically, the neighbor isn’t required to trim/maintain vegetation originating in their property and encroaching yours...same amps with tree limbs.

Here are a few that I'm using.1) Use pine trim instead of MDF.  

I united the cosmetics by painting some of the trim work the same color.  

Unless they eat the trim ,nothing will happen.

We typically use the 3.5" because it's the lowest cost, but for higher-end stuff, we'll use wider, as it's more "in style" (according to the wife).Our main rationale for solid wood is that it can be site finished, which means we can install it earlier in the process (before trim, which is the best time in my opinion), but you can finish it at the end so that it doesn't get scratched up during the rest of the rehab.