Rather than your contractor giving you one invoice for $6,000....do them in "phases" of #1 gutters & downspouts on one invoice ($1000) #2 the vinyl siding on another invoice ($2500) #3 landscaping & trim removal on another invoice ($2,500), etc. 

My demographic renter pays $800-1200 per month and is a late 20s/30s/early 40s and is responsible with a job (bartender, waiter, young professional, etc.).

This demographic of newer investors don't have the time or desire to do the day to day.

Personally I think it has much more to do with the demographics of your rental area.

And we have 2-3 demo guys who can do a lot of different things, like demo, landscaping, picking up materials, etc.

Wash the exterior siding and the roof, fresh paint, good realtor with professional photographer, clean up landscaping, fresh mulch...Clean as can be inside, wipe baseboards, clean blinds, etc. 

But isn't there some way that some of those area/demographic data points show up in your $$$ numbers?

Lighting, doors, windows, exterior painting/siding, roofing, mechanicals, landscaping, demo, permits

Just me, but I would write off the mulch and flowers as basic landscaping costs.

It isn't as cityish as Worcester, but is more of a city vibe than all the surrounding towns because of the demographic.