Task: Sum to 100
C: 

#include <stdio.h> 
#include <stdlib.h>


#define NUMBER_OF_EXPRESSIONS (2 * 3*3*3*3 * 3*3*3*3 )
enum OP { ADD, SUB, JOIN };
typedef int (*cmp)(const void*, const void*);





struct Expression{ 
    int sum;
    int code;
}expressions[NUMBER_OF_EXPRESSIONS];
int expressionsLength = 0;
int compareExpressionBySum(const struct Expression* a, const struct Expression* b){
    return a->sum - b->sum;
}

struct CountSum{ 
    int counts; 
    int sum; 
}countSums[NUMBER_OF_EXPRESSIONS];
int countSumsLength = 0;
int compareCountSumsByCount(const struct CountSum* a, const struct CountSum* b){
    return a->counts - b->counts;
}

int evaluate(int code){
    int value  = 0, number = 0, power  = 1;
    for ( int k = 9; k >= 1; k-- ){
        number = power*k + number;
        switch( code % 3 ){
            case ADD:  value = value + number; number = 0; power = 1; break;
            case SUB:  value = value - number; number = 0; power = 1; break;
            case JOIN: power = power * 10                ; break;
        }
        code /= 3;
    }
    return value;    
}

void print(int code){
    static char s[19]; char* p = s;
    int a = 19683, b = 6561;        
    for ( int k = 1; k <= 9; k++ ){
        switch((code % a) / b){
            case ADD: if ( k > 1 ) *p++ = '+'; break;
            case SUB:              *p++ = '-'; break;
        }
        a = b;
        b = b / 3;
        *p++ = '0' + k;
    }
    *p = 0;
    printf("%9d = %s\n", evaluate(code), s);
}

void comment(char* string){
    printf("\n\n%s\n\n", string);
}

void init(void){   
    for ( int i = 0; i < NUMBER_OF_EXPRESSIONS; i++ ){
        expressions[i].sum = evaluate(i);
        expressions[i].code = i;
    }
    expressionsLength = NUMBER_OF_EXPRESSIONS;
    qsort(expressions,expressionsLength,sizeof(struct Expression),(cmp)compareExpressionBySum);

    int j = 0;
    countSums[0].counts = 1;
    countSums[0].sum = expressions[0].sum;
    for ( int i = 0; i < expressionsLength; i++ ){
        if ( countSums[j].sum != expressions[i].sum ){
            j++;
            countSums[j].counts = 1;
            countSums[j].sum = expressions[i].sum;
        }       
        else
            countSums[j].counts++;
    }
    countSumsLength = j + 1;
    qsort(countSums,countSumsLength,sizeof(struct CountSum),(cmp)compareCountSumsByCount);
}

int main(void){

    init();

    comment("Show all solutions that sum to 100");            
    const int givenSum = 100;
    struct Expression ex = { givenSum, 0 };
    struct Expression* found;
    if ( found = bsearch(&ex,expressions,expressionsLength,
        sizeof(struct Expression),(cmp)compareExpressionBySum) ){
        while ( found != expressions && (found-1)->sum == givenSum )
            found--;
        while ( found != &expressions[expressionsLength] && found->sum == givenSum )
            print(found++->code);
    }

    comment("Show the positve sum that has the maximum number of solutions");
    int maxSumIndex = countSumsLength - 1;
    while( countSums[maxSumIndex].sum < 0 )
        maxSumIndex--;
    printf("%d has %d solutions\n", 
        countSums[maxSumIndex].sum, countSums[maxSumIndex].counts);

    comment("Show the lowest positive number that can't be expressed");
    for ( int value = 0; ; value++ ){
        struct Expression ex = { value, 0 };
        if (!bsearch(&ex,expressions,expressionsLength,
                sizeof(struct Expression),(cmp)compareExpressionBySum)){
            printf("%d\n", value);
            break;
        }
    }

    comment("Show the ten highest numbers that can be expressed");
    for ( int i = expressionsLength-1; i >= expressionsLength-10; i-- )
        print(expressions[i].code);
    
    return 0;
}

Python: from itertools import product, islice


def expr(p):
    return "{}1{}2{}3{}4{}5{}6{}7{}8{}9".format(*p)


def gen_expr():
    op = ['+', '-', '']
    return [expr(p) for p in product(op, repeat=9) if p[0] != '+']


def all_exprs():
    values = {}
    for expr in gen_expr():
        val = eval(expr)
        if val not in values:
            values[val] = 1
        else:
            values[val] += 1
    return values


def sum_to(val):
    for s in filter(lambda x: x[0] == val, map(lambda x: (eval(x), x), gen_expr())):
        print(s)


def max_solve():
    print("Sum {} has the maximum number of solutions: {}".
          format(*max(all_exprs().items(), key=lambda x: x[1])))


def min_solve():
    values = all_exprs()
    for i in range(123456789):
        if i not in values:
            print("Lowest positive sum that can't be expressed: {}".format(i))
            return


def highest_sums(n=10):
    sums = map(lambda x: x[0],
               islice(sorted(all_exprs().items(), key=lambda x: x[0], reverse=True), n))
    print("Highest Sums: {}".format(list(sums)))


sum_to(100)
max_solve()
min_solve()
highest_sums()