Alright I am new here and I saw that you guys actually reply to people,

I am trying to figure out how to replace my windows in a house I bought last
year.

The windows I have now are pretty much wasted, the previous owner decided to
paint them without removing the old paint, re-glaze without cutting the excess
glaze of, and also painted EVERY single surface that should never be painted
(rails, etc.).

I have 24 windows that will need to be replaced so even doing it cheap is a
load of money.

My question is can I use replacement windows or do I need "new construction"
windows.

also I am sorta confused about how to finish the outside: as should i use
brick mould w/caulk or aluminum? I have looked around at other peoples houses
and a lot of them have what looks like colored sheet metal around the outside.
And some sort of grey caulking, I've seen this caulking on about every brick
building i have looked at and I do not know what it is.

In one of the photos below I pulled the brick mould off to see what was
underneath, expecting to find the edge of the window frame, but found a 1X4....

any help or advice would be appreciated.

Judging by the storm window hangers in one photo your house is a few years old; probably at least 50. New aluminum clad windows would not be in keeping with the style of the house.

I'd scrape and patch and paint. Even if there are multiple layers of paint you can do a little scraping and these windows will look better than anything you will buy today.

If you are worried about energy efficiency, you can get some storm windows or even spend a little time making the existing double hung windows more weather tight. It takes a long, LONG time to recover the cost of new windows in fuel savings.

An excellent book on maintaining old windows is 'Working Windows' by Terry Meany. You can get it at several on-line booksellers.

I know this will be a minority opinion. I also suggest you give very serious thought to keeping those windows. You can also add an insulation strip to the inside of that great storm window to decrease any air infiltration.

Please price a wooden replacement window, installation, and new storms. Compare that to the cost of restoring your windows. An energy audit will help you determine where you have heat loss in your home. It is incorrectly assumed that simply replacing windows is the answer to energy conservation in older homes.

Debbie
(If i can do a window, anyone can.)

The windows are actually in pretty good shape and do not need much work.

You can probably use either type of window, though to be honest, it's always harder than window companies describe. I just put in a couple of Marvin Infinity windows (fiberglass insert replacements) in our 50 yr old house, and I must say, they look a h*ll of a lot better than the original wooden junk with aluminum triple-track storms. And they work.

The standard advice for which type to use is to look at the frame condition. If they are rotted, or out of square, they should come out, and new construction windows go in. A pressure treated frame can be built inside the opening if it is a masonry house. If they're not, you can use inserts, which are available in wood and fiberglass, too.

The outsides were originally wood, and then sometime later someone added aluminum casing to them. This is what you'll probably have to do also. You can hire someone to do this for you, or the window company can do it, or you can get the tools & materials to do it yourself. The caulking is fairly standard stuff that is usually paintable.

I don't know if in the end this will be much quicker then restoring the old ones, but you'd probably like everything to match. Either way, you're looking at a good bit of $$$. I'd probably hire this job out to a company that makes the window style you like. Or do a couple a year, like I am!

Or you can anchor te windows nto the masonry using tapcons and not loose the opening size (1.5 inches each way).
Lining the opening with wood os a shortcut used when the installer does not know how to anchor to masonry.

You are going to have to decide where your budget is taking you. Wood, wood clad, glazing, etc, along with the quality of product you are willing to invest in.

I would be looking at both functionality and energy efficiency. Installation procedure is going to depend on manufacturer, and the construction of your home, which is not visible in your photos. You may be best served by using a manufacturer who provides a turn key solution.

Paul