I recently acquired a new rental property.  It was built in 1910, and there are a lot of things I like about it.  It is currently in a C type neighborhood, but things are improving, and I think it will be a B property within 5 years.  Possibly even an A property in the distant future.

I have one issue I would like to get some ideas on.  

All the woodwork in the property has been painted brown.  This brown paint was applied over a cream color paint with a gloss finish, and the brown paint does not adhere well to the cream.  You can scratch it off quite easily with your fingernail.

I am assuming there is no good fix for this, and this will be an issue going forward at every turn.  I have some idea, however.

• 
  Paint it brown.  
  • This way, it will not show dirt, and at each turn, when I get it ready for the next set of tenants, I can just touch it up.  It is, however, not a pretty brown.

• Do good paint prep, and paint it cream. 
  • Maybe if I do the prep work properly, the new cream paint will stick to the brown paint, and when the brown paint comes loose, it will simply reveal more cream paint.

• Somehow remove the brown paint.  (I am assuming this is quite problematic, because it is quite likely that much of the trim paint is lead based.  I have even wondered about cheap masking tape.  I know if you buy cheap masking tape, and leave it on too long, it will adhere too strongly to the paint below and will pull it off.  Perhaps this aspect of cheap masking tape would allow it to be used as a solution to this problem, leaving it on too long and then pulling off the unwanted brown paint.  

Any ideas?  

Its not a fun issue , but I deal with it constantly.

What happened is the  Pink paint below the brown paint is probably an oil base paint and the brown paint is a latex based paint!

The pink paint should have been lightly sanded and then a good primer but it didn't.

So now you have paint that every time get nicked it shows pink!

I would just touch up each time.

Or you can remove trim and jambs and start over about $250 a jamb!!!

Sand, prime, paint...ugly process, great results.  

And - WEAR A MASK when sanding and vacuum, don't sweep, afterwards.  Lead Based Paint was used until 1978.  

Perhaps sanding it down first. Then do your paint prep/painting.