Would love peoples input. Company does a very good job, offers 7% discount if paying cash. Are these prices in line with others who hire professional landscapers?

Total is 11050 USD - 7% for cash. Live in MA, 0.45 acres. See pic below:

$3,150 per week for mowing and tidying up, for less than half an acre, is insanity! It doesn't even need mowing every week. They will mow the heck out of it until it turns brown and then charge you to resod the entire lawn.

The quote is poorly written but its about ~120 per week!

LOL, that’s a relief!!!!! I read it a few times, thinking, “Is that really what they mean?”! However, most lawns absolutely do not need weekly moving during the summer. Every year I watch over-mowed lawns browning out.

The only way you'll know if it's a "fair" (market) price in your area is by getting two other quotations.
The only way you know if it's worth it to you is by estimating the hours it would take you and your value per hour (plus equipment).

We only have around half the space in a VHCOL area but decided that gardeners were too insanely expensive and also didn't give us what we wanted. They are obsessive about removing leaves and twigs and making things look manicured. They are average at keeping your lawn healthy (unnecessary de-thatching, over-mowing, poor quality seed), use way too many [IMO unnecessary] chemicals And they are not expert are pruning the plants.
Really what we wanted was a gardener, which could recommend and plant good native species that don't need too much help because they evolved for our climate & soil, then prune and mow a little, have a nuanced approach to wildlife and weeds. That's not a service we could find near us unfortunately.

Also in MA and similar to what I was paying. Have about half and area and weekly mow was $55. Spring and fall cleanup was roughly $650. I went the other way and stopped it all 2 years ago. I now cut grass myself, but typically only every 2-3 weeks. Didn't do fall cleanup, just left the leaves on the ground. Most have blown away.....

I do my own at my primary residence. CAPEX was high to start (mower, snow blower, backpack leaf blower, edge/string trimmer, chainsaw, tree trimmer, hedge trimmer etc… but annual OPEX minus my time is low (I will do around 1h a week in average) . Basically some car gas, a filter and oil /spark plug kit and the premix for small engines ($100 a year total) My secondary residence is 1h drive each way so I have it taken care off, including snow plowing, mowing, edging, fall cleanups, clearing gutters before winter and some minimal fertilize. I am on well water so do chemical weed weed killer. The only things I do are bark mulch and cold patch road maintenance which I do my self. That’s maybe 8h of labor and $200 in material. I was quoted $1000 to weed and mulch (which I assumed, I don’t want the job pricing). For the rest I pay around $2,400 a year.

The primary lawn got to compacted during construction of the east wing and new deck last year so I am doing aeration / power seed and fertilizer treatment plan this year, that’s around $1600 and 5 organic rock treatments are another $600. This year I will also starting to migrate to 60v electric for all the yard equipment, they are all now 9 years old. So expecting $2k over 2 years , will keep snow blower as gas.

Do you have a 100 acre yard?

Granted this is in Mississippi but we pay $80-$100 every 2 to 3 weeks for mowing 3/4 acres, trimming hedges and bushes when needed, edging front and back and removal of debris.