[Lalamcd23]

My old window trim has so much caulk and wood filler from the previous owner of our house that I don't even know where to begin to repaint the trim. I removed the blinds because I wanted to make the kitchen feel more open but now all the flaws are so noticeable. I'm trying to fix up the house to sell and would really like to be able to leave any window coverings off. How much work would it be to just replace trim? Or should I just attempt to fix before I repaint again... The walls are plaster...

 

[cibula11]

If you haven't done trim before I wouldn't practice on a house you want to sell unless you're comfortable with this type of carpentry. Not sure of the
age of your home but if it's older I'd be even less likely to replace the trim. Get a good paint scraper or something relatively sharp and start scraping and knocking down the rough spots. Come back with a sanding block to smooth it all out. ( be sure you're not sanding lead based paint first) finish with satin paint, anything glossier will show the imperfections.

 

[joecaption]

For detail work like that I use my ossilating saw with the sanding pad.
Whole lot faster easier, cheaper to just sand, prime and paint.

 

[ChuckF.]

Doesn't look that bad from here. Sand and fill the rough spots, repaint and then put the blinds back.