I know this is long, but I could really use some advice =)

I like to think I'm a smart guy, but new windows (and the quotes) are driving me nuts. I've had 2 contractors over for quotes, and I'm almost ready to call it a day. May some of the experts here can offer me some advice.

The house basically has three types of windows:

-vinyl double hung (upstairs) with original farmhouse trim. All the same size.

-metal double hung (living room). Mostly the same size.

-Wood casement (original Marvins from 1950's)

-Technically a fourth type.......huge, double-pane fixed with great view (see below).

Here is a small sample of the windows:

Upstairs

Downstairs (2 large ones + 1 single casement, 3 wood double hungs)

Metal windows

Wood double hungs downstairs (I'm considering making this one large casement window. Contractor #1 could do this)

Quotes I've Received

1. Contractor 1 - Came recommended from another contractor as he has old home restoration experience. He was a home builder back in the day, but does a bit of everything now (additions, remodels, etc). He isn't strictly a windows guy, so when I mentioned I wanted to do new construction windows for all 26 windows, he said no problem. I think he offers more flexibility if i wanted to combine 3 double hungs into a large casement or add a new window somewhere.

I don't if this was a communication issue, but he quoted Andersen 200 series at about $400/window + $425/window labor. So about $900/window (new construction). I don't think he cares what window I go with (see below). I haven't got references yet. I know I'm not going with 200's.

2. Contractor 2 - Met him at a large home show, he was in the Marvin booth. Checked him out on Angie's List and he had nothing but great reviews (e.g. not the cheapest, but attention to detail, good quality work).

He came over this week and measured every window. Originally he recommended Marvin Ultimate, but since the upstairs is white trim, he recommended going with Andersen Woodwright (400's?) drop-in windows in white. This leaves the trim. He said drop-ins would be better because the plaster upstairs is iffy (and newly painted).

Downstairs he recommended the metal windows and casements be replaced with new construction Andersen Woodwright's. For the 3 wood double hungs, he recommended drop-ins (Woodwright).

He seemed knowledgeable and has been doing windows for a while. He recommended a 2wide/1high grille (for the DH's) as that was the farmhouse style. I'm waiting for a quote from him.

Concerns/Questions

1. How much window room (area) will I loose with drop-in windows? I love sunlight and bright areas, so I'm concerned drop-in's will reduce window space. On the other hand, the original trim will remain for upstairs (if I go with guy #2).

I don't want them to look crowded like this:

2. Should I try to keep the trim?

-The upstairs is white molding.

-Downstairs is white 1"x4" square trim.

-The metal windows don't have trim, though baseboard is stained.

-Baseboard throughout house is white.

Originally I was shooting to keep the upstairs trim and replace the downstairs trim with stained 1" x 4" trim. But does the window trim (stained) need to match the baseboard (white)? Because if all the drop-in's remainining white and the new construction's stained, the house will have a mishmash of white and stained trim. Ahhh....

3. If I go with Contractor #1, I can probably choose Andersen 400's or Marvin. Are there other windows I should consider?

4. I didn't know this, but a window install doesn't include staining the windows or trim. Should I consider having them stain? I've never done this, but would be up for it. My concern is boths guys will stain them quick and dirty (one coat of stain, 1-2 coats of poly, no sanding, etc).

5. I'm thinking about combining two sets of windows.

-Turn the three double hung wood windows into a single casement window. Bad idea?

-Covert two of the metal double hungs (not pictured) into a single casement. This would give me two part windows in the living room with great views.