We have an old cherry table that my wife wants to paint. I'm not keen on painting stained wood, but I want to keep her happy. Is there a way to paint stained wood to make it easier to strip again later on?
Paint it with a waterbased paint*
These are usually much easier to strip at a later date than oil-based paints, which in the present day are usually some type of enamel even if the labelling doesn't describe them as such.
There isn't a huge amount in it but a more-matt paint (semi-gloss down to fully matt) will generally strip slightly more easily than a gloss paint, as the former have a more 'open' surface. So if you don't mind that the table isn't full gloss when painted there is a slight advantage later on.
Paint it with oil paint
I mean linseed-oil paint specifically, not any old oil-based paint. Without a resin component (this is what turns oil paint into an enamel) plain oil paints remain much more responsive to solvent stripping, almost permanently.
There are some additional points worth touching on.
Clean the surface before painting
Normally you'd want to clean the table thoroughly and lightly sand/scuff it to promote paint adhesion, but here I'll specifically advise you to skip the scuffing. You still need to clean the surface well so that any contamination, especially furniture polish or wax but also possible residues of cleaning agents, are removed as these could lead to defects in the paint film.
Since the wood is already stained it is likely also varnished or lacquered so I don't see any benefit to going the extra mile and using a barrier coat. If the table were bare wood however it would be well worth giving it a single coat of shellac before the paint went on.
*But not milk paint! Milk paint is famous for just how difficult it is to remove once cured — most conventional paint strippers have zero effect on it.
Depending on how durable you want the finish to be and what you want to do later, one thing you can consider is to seal the wood with a clear shellac or polyurethane before painting it. After that, you can use a latex paint over the top. The latex paint won't bond well and will scratch easily, so it will not be the most durable finish.
The sealed wood will not absorb the paint, so it will be easier to remove later.
If you later want to stain the wood, you'll need to strip the paint and sealer, which could end up being as much work as just stripping the paint, so like I said - it depends on your future plans.
They make coatings that are more in the family of "dip tool handles in this stuff"... but are often pitched as semi-permanent paint with removability. They can be peeled up with a bit of work.
Since it will all be under paint anyway, you could make a similar piece out of ... not cherry? Who would know under the paint?