You must have paid without inspecting the work. Building code requires a weather barrier under the siding and that it be taped at openings and all seams. Was there a permit obtained to do the work? If not, did your locality require one. If they did, report the contractor to the inspection department  as having not pulled a permit and gotten the right inspections. They may be able to help you and it oculd be a license violation in your state. Although most will refuse if a permit was not obtained and the proper inspections performed. Maybe they will go after the contractor and have them make it right. Have you checked your ceiling insulation? Heat rises and if the attic is not properly insulated(This is where 2/3 of the heat escapes from a house.  and  the soffits(overhang)need to be  vented. Heat will escape through the roof. How about your windows. Caulking around the j- channels where it meets the frame may stop some air and water infiltration.Do this with a clear caulking made for that purposed.  A lot of heat escapes through windows if they are not properly sealed. You may be able to put some plastic film over the windows and inside casings like 3-M. This may also help you with heat loss. There are foam inserts that you could put in the electrical outlets by removing the cover screw ,,pulling the cover,  putting them in place and then puttng the screw back in. Maybe the walls should have been insulated while you had the siding off. There are many things you havent't told us but these are ideas that may help your situation. It sounds like you do not have a foundation with blocks. But they are also a souce of heat loss. If you do, you could insulate the rim joists with a high density foam sheet and cut them to fit. and then use caulk or spray foam to seal around the edges. Hope this helps you.  

Doing a water test to determine where the water is entering may locate the issue.  Also checking your roof vents, flashing, chimney, gutters and downspouts

Are you asking how to repair or solve the problem?  Always need to look at flashing gutters and downs and roof penetrations to locate the leak.

Besides the painting suggested by Chad of Lonestar Painting which can truly makeover the appearance of a home, I suggest that the trees and shrubs be professionally trimmed and thinned out.  Application of weed control and fertilization of the lawn will provide a healthy and attractive canvas to your yard that can be supplemented with a dose of spring color annuals

A very quick and cost effective way to upgrade your homes exterior is a cleaning and color change. Pressure wash to clean it up and paint the shutters and front door.  They can remain the same color or pick a fresh new color.  You can also take any old fixtures that have faded over time and paint the metal with a fresh satin or gloss paint.  Same with metal railings or metal awnings. Possibly a one day job with big results. 

Yes, you need to contact a roofing company to check it out.  Possibly need a rain diviter installed.  Possibly need a gutter installation company to swap out current gutters for larger commercial size gutters.

Tear off cimney from roof, cover plywood hole, and install roofing to match

As a basement finishing company we're seeing a lot of granite for wet bars, lighter colors. Bathrooms and tile are often favoring gray. Brushed nickel and steel are the most common hardware and fixtures. Clean,simple, easy to mix up with rustic or modern decor.

We're still seeing a lot of demand for granite and/or quartz countertops.  With the quartz, people are doing more subtle patterns and a lot of marble looks (white with light veining or similar).  Cabinets seem to be following a gray/neutral/white color palette, with lots of clean lines.  We're still seeing stainless steel and brushed nickel for appliances and hardware, however we saw quite a bit of matte brass and gold tones at KBIS this year.  That seems to be making a comeback, but I think that might still depend on your area.  I think oil-rubbed bronze is probably on its way out, unless you're doing a rustic look.  Hope that helps!    

Yes A mason with some old school skills.

I guess this would be called a remodel:  what is happening is the valley gutter is draining down the side of my house presently.  I would like a large "basin" type catch to divert the water away from the siding.

If you want an efficient fireplace, I recommend a full insert (sealed-combustion) that runs a new vent pipe, typically up your existing chimney. Hire a professional installer from a local fireplace company to do this. 

There are also options to retrofit a "gas log" in an existing fireplace, but there are several issues with this. Typically, if you have an open hearth without doors that seal tightly closed (with a gasket) then you are going to put more energy up the chimney than actually radiates out into the room.

Brick mason

Both, more than likely. The mason should replace the masonry products and the roofer should work with the mason to achieve a regletted counterflashing and flash the roof under counterflashings.