What kind of condo is it, specifically, is it an apartment in a larger, older, masonry building?

I have a pretty reliable Masonry that I use I can send over his information. 

It takes a considerable amount of skilled and reliable labor to complete 25 homes, so we suggest subcontracting all the trades and retaining a small in-house crew of experts in individual trades such as framing, masonry, roofing, etc.

His company is Bullseye Real Estate We've used him mostly for small scale repairs, i.e. build a bathroom, repair the roofing, patch drywall, paint, kitchen install, masonry repair (front steps) etc.

An experienced inspector who's only inspected 1960s masonry homes in the desert southwest isn't the most qualified to inspect an 1870s wood frame house in the northeast (and vice versa).In addition to many years' experience inspecting, you ideally want an inspector who has a background/experience in engineering/building/contracting.

All the rain and the freeze/thaw cycles speed up the degradation of masonry work, wood work, paint, and can cause many other issues that don't occur as often in warm, dry climates.Regarding your appreciation estimates: in a C or D area, you may or may not get 3% property and rent appreciation--lots of C and D areas depreciate (without a LOT of data and research, it's impossible to know what the future holds...and even with a lot of data and research, it's impossible to know what the future holds!). 

For a rental I I'd take it out unless it was masonry siding, that way I never have to worry about it again.

Again look where the wood structure meets the stone or masonry foundation for these issues.

As well as various decorative masonry elements, when the tech gets that far.

We are thinking either construction adhesive on the wood with penny nails hammered through into the mortar to hold the boards place while the adhesive is curing, or to drill Tapcon masonry screws through the boards and into the brick while being really careful not to over-torque and bust out the brick...