I’m not sure if it’s worth the expense to demo plaster and hang drywall (or, maybe hang drywall over the existing walls?)

Single Story 3 bed 2 bath 1585 sqftPaint Interior - 1585 sq ft - $1.9/sq ft = $3,000Scrape popcorn ceiling, texture, and paint - 1350 sq ft - $3.1/sq ft = $4,185Remove old carpet and install vinyl plank flooring - 1175 sqft - $5/sqft = $5,875Replace carpet with new carpet - 410 sq ft - $2.2/sqft = $910Remove dead grass and install sod - 1850 sqft - $2.1/sq ft = $3,850New two car garage door/opener/track and installation = $1,500New window and installation = $250 eachBathroom remodel - vanity, mirror, light, toilet, demo and build back new tub or shower with ceramic tile - $4,500Kitchen remodel - 30sqft quartz, 12ft upper cabinets, 12ft lower, backsplash, sink/garbage disposal, $9kThere are many more items to be repaired/replaced but I realize this is turning into a long post so I will stop there.

Brandon this is about a 7-8 mos. project for us - to flip the entire building over and renovate it and get it back online with new tenant pool of occupants - I renovate as many as I can simultaneously, just set it up like a conveyer belt and move through them in sequence:*Demo team - remove all old fixtures, flooring etc, cut out all tile in whole sheets - then they set the new cement board and get the drywall hung and taped, set the new plumbing rough-in valve*Flooring and Tile team follow - get that installed with the new shoe mold on the perimeter*Painting team follows*Finish team returns for all fixture and finish install - *Painters complete touch-ups if needed *Cleaning team - BOOM!

Sometimes we just need help with labor, like carrying lumber or other heavy items, or demo work and moving out trash. 

This looks like a after thought and could be demo and patch with some plywood and siding that matches.

To frame in the walls will take 2 guys about 2 days to demo the garage door and frame in the new one (that's being generous).  

Option 2, get an oversized blade on a demo saw and cut half way through from each side.

I did demo a 2 storey house and 1 single storey plus cmu wall fence, I burned 35 40yd dumpsters and 22 low-boys.

Very likely you wouldn’t want to do much before moving it— I might not even demo it (if it needs it), as sheet rock can help w structural...Pursue it, though, and get lots of bids and do your due diligence — because the numbers might work well, and most people would be too timid to take it on!!  

They will not issue a building permit, it seems, until the process is gone through the right way.Maybe it is like this everywhere, maybe it was particular lots we dealt with but demo is not demo without the permit.If you want to PM me the address or post the part of town here without specifics I can tell you a little about the area if that would help.