Dissolve it up in THF or whatever solvent you’re using to make the enolate as a dilute solution (e.g. 0.2 M)

Why not just pre-form the enolate with LDA in THF and then add your aldehyde dropwise at low temp? The OH could end up protonating your enolate, but it’s pretty sterically hindered.

In that case, it would be hard to protect since it’s sandwiched between those t-butyl groups.
Have you tried running the reaction anyways? Do you pre-form the enolate of acetophenone and then add the aldehyde? Curious if the OH would give you problems.
Otherwise this is basically a Claisen-Schmidt reaction, of which about a billion examples exist, under conditions where the enolate forms reversibly and a slight excess of base, I would imagine you could get this to go.

Which hydroxybenzaldehyde are you starting with?
The usual procedure would be to start with a methoxybenzaldehyde and then try to remove the CH3 after your aldol with something like TMSI.

One milder way to do it would be to treat the hydroxybenzadehyde with KH and BnBr to make the O-benzylated benzaldehyde and then after your aldol, treat with Pd-C, H2. Or paramethoxybenzyl (PMB) and deprotect with DDQ.

Without knowing what your molecule looks like it’s hard to say. It would be easy to selectively protect the aromatic OH because it’s considerably more acidic, and once you form the alkoxide it will be far more nucleophilic. One idea would be to just protect both groups, and then selectively deprotect the aromatic OH afterwards.