Need a bit more on how the compressor is failing. Is it seizing, or is it electrically burning up. The reason for this is that with the relocation to the dog house to the roof (a good move) you need to have the suction line redesigned properly (oil trap … google refrigeration oil trap) to get the oil return to the compressor, this would result in a seize of the compressor if not done. If it is a true burn up, then there is residual acid in the system, this may not seize. Put a new compressor in, and not treat the acid problem and the new compressor will be dead in a year from residual acid in the system.
Acid remediation would be a suction line filter dryer and a liquid line filter dryer. (Some techs prefer just an oversized liquid line filter dryer) but it needs to be a filter dryer that can deal with acid, like an Emerson EK series. Good practice after a burn up, is new oversized filter dryers. Then back in a week to do an oil change and test old oil, (hard and expensive on hermetic unit as you must break the system open and remove compressor to drain oil), replace liquid line filter dryer, remove suction line filter dryer, and fill with new refrigerant. I would come back in a year and do it again, at least test oil, change liquid line filter dryer and new refrigerant. If oil tests bad, then another oil change. The acid lives in the oil, and the oil circulates in a refrigeration system. Burnouts are a real pain to get the system clear of acid. But it is necessary to get back to the original life time. There are some “treatments” (chemicals to add to neutralize the acid), but not widely used.
Then there is the possibility that the refrigerant was changed when the dog house was installed. Was there a change from R-22 with mineral oil to a “new” refrigerant like R-404A? If such a change was made, there needed to be an oil change to Polyol Ester Oil (POE).
Lots of stuff going on. At least I gave you a few questions to ask your tech. If he does not converse well with you in these areas, it’s time to get another service company on your equipment.