Here's a wider shot, somehow it didn't make it into the original post.

The primary challenges here:

body of brick is darker than roof leading to "hats' off " feeling - painting brick a light off-white tone like bm collingswood http://www.benjaminmoore.com/en-us/paint-color/collingwood
would make a big difference positive - one might mask out the sill bricks and paint them a bit darker like northern cliffs http://www.benjaminmoore.com/en-us/paint-color/northerncliffs - at the lower windows, paint the wood trim cap the same northern cliffs tone

shutters are too small to actually close, so they look out of proportion. Just take them off for now

Paint the portico face the same collingswood and let the trim at the eave and posts remain the same crisp white as the eave and fascia board above but add one coat of creamy white like sw dover white. Underneath the arch, / ceiling of porch should also go to collingswood.

Front door should ideally / in long run be replaced with classic door plus two sidelights. More light gets into the entry and the door proportions are improved. Then you might paint all the trim and sidelights creamy white and paint the entry door a crisp bright navy tone - like sw commodore http://www.sherwin-williams.com/homeowners/color/find-and-explore-colors/paint-colors-by-family/SW6524-commodore/ or bm patriot blue For now, paint them both a historic dark red like sw rookwood red or bm tea http://www.benjaminmoore.com/en-us/paint-color/tea

Trim the hedges low so all the window sills are apparent. Plant flowers between bushes and liriope / groundcover adjacent to path. lots of bulbs in between after you trim back should work . .

If he wants to keep the brick, or has to replace the roof anyway, get a charcoal roof - most versatile for long term. Lose the shutters still but paint the doors in an sw urbane bronze tone to echo the aluminum windows. Change all the white trim to a deeper tone like http://www.benjaminmoore.com/en-us/paint-color/nantucketgray - it will coordinate better against the brick tones or even go blue-gray like bm black pepper.


If he replaces windows, please use three single/double hung where the two pane sliders are now for historic cred / restored charm. Get muntins / grilles but only on the top half for a custom window look. If he is considering vinyl windows, he will need to paint the brick - white vinyl will never look right next to the dark brick.

It looks like a four unit apartment building.

I like the house!
Here are some photos from Houzz for ideas. Paint seems the easiest, so maybe it just needs
1) more white added by painting the window trim.
2) Or instead of white colour, paint the window trim and all porch columns etc. taupe.
3) paint front door black. I think this will do a lot!
4) paint eavestrough of roof also, maybe black or taupe....

Painting brick can (but does not always) cause eventual structural damage. I would personally not do it.

Aesthetically, I think the house isn't awful but some of the colors are. I would remove the shutters and paint the white parts and the green parts something more closely related to the brick in color (brown, rust, dark grey, etc.) Then, I would hire a garden designer to help plan new landscaping that was less solid-looking, and more garden-like. You can always implement that in stages as money becomes available.

This will be a beautiful house! The wide, sweeping lawn and nice entry just need a little tweaking. Understatement is key here, it seems to me. Since the roof is pale grey, I'd replace the white trim with a slightly darker gray, ditto the portico. Do the front doors black, with kickplates and hardware that match in silver. Spray paint the existing lights by the door to silver, as the black doesn't seem to show up much. Remove gigantic bubble shrubs. Remove dinky shutters. Two classically styled urns of some size in the entry area. Put traditionally styled house numbers in black at the top of the entry arch. Repaint the fence in a soft gray rather than the tan color. There's much more you could do, of course, but these seems the simplest remedies.

I like the house! I'm not sure what the roof is or the color, but some sure curb appeal would be to ditch the green shutters and paint them to match the portico...paint the door a different color, something in the tones of the brick color?? From a landscaper's perspective, ditch the shrubs! They really date the whole look of the house. You could do a lot with adding some height in the landscape, birch trees, for an example. The height can draw the eye away from the roof as well. Also, define the walkway...there is this fabulous portico but the feeling of an "entrance" is lacking. Just my thoughts, good luck!

Trim up the shrubs, and the foundation plantings wouldn't look half-bad! Looks like a great buy (but IMO don't paint the brick -- that's a road to constant maintenance headaches).

PRO
Sweet Caroline Garden Design
Nice house which could be made nicer with a little paint and landscaping. I would trim hedges below window height and then trim the outer taller ones as in my doodle below. If there's room two containers of seasonal color under the portico and in the front flower beds would look great. I would paint the portico and trim a glossy black and the door a blue gray to match the shutters Below is an example of the blue and black against red brick..

Oh my goodness I just came to see if anyone had commented, and I'm blown away! Thank you everyone for your amazing responses, I can't wait to share them with my dad! I'll try to report back with his opinions/decisions later today or tomorrow.

Staining brick is ok and more permanent - should have mentioned that option above.

Ok, I've shared all of these ideas with my dad, he's amazed at how many people have chimed in. Decisions thus far: We're definitely going to trim down the bushes up front, and replace the double doors with a single door and sidelights. By the way, this house is a short sale, so while he's put in a contract things are now up to the bank and their timelines.

Excellent! Dad thinks kid is a genius, right before Christmas!

As far as trimming those bushes, to be honest, by the time you trim them down to a decent size they may or may not come back. In general, taking a shrub down by more than 1/3 in any one year isn't such a good idea, and these need way more than that. They can live on when recycled. :)

I am not sure where you are located, however I cut back my large, hollow, 30 year old camellias by doing the following: In fall, prune all the branches to the main trunk, except for branches at the top. In spring, cut the top to the level that you want. This keeps the plant from going into shock

In the case of your evergreen bushes the 1/3 rule can work very nicely with a different spin. While dormant (winter) you remove 1/3 of the branches as low as you can- all the way down at the bottom. Allow the plant to recover for the next year. The following dormant season (a year later) you do this again but again cutting the old wood (so now only 1/3 of the old wood still remains). The third year you cut the last of the old branches. Now the plant will be much smaller but obviously it is a game of cutting it back every year or replacing it with a plant that has a lower full height.