Its a cute house. Will be cuter with some plants and landscaping. I would do the windows 1 at a time, and strip them, and remove caulk, and redo them. No hurry, it is sealed against the elements. I would have all the electric checked, and the plumbing checked, since the house was built in 1942. I would want to make sure any knob and tube wiring is removed and replaced, if there is any left. I would want to make sure all the plumbing is checked to make sure nothing is going to leak and cause any water damage, etc. Maybe repaint interior, if needs it. I wouldnt do anything he can live with, until he can actually afford it with out struggling. Priorities are water tight, and safety. He may also want to have the heating and the ac (if it has ac), all checked out too, so there are no surprises when its time to turn them on. A service call for that is always a good thing, just because, they clean things up and keep them in tip top condition.

Truly beautiful home. If the caulking job is functional, keeping water from seeping in, and the only problem is that it looks sloppy, then keep it as is. There are going to end up being things you don't expect that will be way higher on the priority list. Your son should save his time and money for those items.

There is a lot that can and does go wrong with old houses that is all behind the walls and nobody ever sees the labor and dollars that goes into them.

Aesthetics is sometimes a luxury to focus on in an old house if you are cash strapped. But, if it is his forever home, he'll have years and years to get to the beautification stage.

I agree that making sure the water, heat and electric are in good shape is the priority. The house is adorable and the sloppy paint issues can be saved for warmer weather.

If you live nearby, perhaps you can talk to neighbors who share cuttings from their gardens or know where to get inexpensive bushes, bulbs and plants. More landscaping - over time - will really enhance the beauty of this house.

He should be commended for getting himself a great little house he can make his own.

Just thinking out loud….
I am not a professional and have never done this on a stucco house. My first thought is to get a thin molding to edge the door with, instead of stripping it and redoing the calk. Of course, the molding would need to be painted with exterior paint and calked also. Maybe a vinyl molding could be used. Hopefully that would give it a cleaner look.

Unless the house was recently painted *and* you have some extra paint lying around, I'd just live with the caulk. It's not really noticeable. Does it bother your son?

Yes, it was recently painted. It is very noticeable in real life, much more than in the pictures. It does bug him.

A 1942 house may be old to you, but there are lots of much older ones out there. The original construction was probably better than a lot of the fast slapped up crap that has happened since 1942.

Given the house's history (foreclosure, flipped, etc.), I would be budgeting for things like furnace, hot water heater, roof--things that matter. The painting doesn't look that bad and can easily be touched up (if you have any leftover paint).

To me, the planter box is more of a distraction. It looks like it needs to be taken down and re-laid. Since your son is working two jobs, maybe this is something that you can lend a hand with or the painting.