Aloha,
Well, I see a number of issues here.
Starting with the "Notes Recommendation".
Not much useful info there, very poorly reported, hopefully the pics were of more use to understand the issues. Looks more like a handyperson wrote this up..."doesn't look good", "recommend a specialist", "need different vendor", "looks like it can last", "looks like outlet burned out" (yet, he only lists the $20 charge to change the outlet cover), "remove mirrors".
Moving on to the charges, I don't have a clue of your local costs, but first of all, an unlicensed handyperson should not be on the roof; regardless, if he plans to charge you $550 to brush on a little roof cement around the penetrations, way over priced. What, exactly does he plan to do, where on the roof, and why (if not evident in photos)? It is more likely you are nearly due for a new roof due to lack of regular preventative maintenance.
If the chimney sweep is actually a professional, that has the proper tools and knowledge, might be OK, but still seems high. One story or more?
I would want to see the yard cleanup costs separate from the pruning/trimming. Costs will be very dependent on how high the work is and type of equipment needed. You can hire day labor and get a rolloff for the cleanup, let the tree guys do trees. And be sure THEY are pros; too many "yard guys" are just hacks that cause long term damage by improper cutting of desirable trees.
Window well cover? How many, what size, not that difficult to install common basement well covers... typically 5 or 6 screws for what I am picturing, but I do not know what you actually need. Price the covers at HD and guesstimate from there.
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Installing sheet vinyl...cheapest possible choice, guaranteed more work for them in a few short years. You probably do, or will have, a mismatch of flooring from one room to the next. You do not indicate the quality of the unit, but from what I am seeing in the repair list, seems low end, to low average. I stopped using sheet vinyl in low end units over 20 years ago. Armstrong commercial vinyl tile works well once you source someone that cleans and waxes it properly. Luxury Vinyl Plank has come a long ways, and is pretty easy to install. Looks fantastic when you have one continuous flooring throughout, no matter if CVT or LVP. Both will last AND look far better for far longer than sheet vinyl. Be sure they pull the toilet to install any floorcovering, and do NOT caulk the toilet base to the flooring.
Reglazing the tubs, while priced right, tells me this is an old property. Reglazing is fine, looks great, but again is a short term fix. If Tenants are not properly instructed in proper care; if they dump draino in/around the drain; or if the tech does not properly prepare the surface, they will last three years or less, and get ugly much sooner. The bigger issue however, is the age and condition of the drain and waste line, as well as the supply side lines. At this age, they are probably at or near the end of their life as well, and if either has slow seepage, it will be damaging your subfloor and structure until someone notices and reports an "unexpected" leak. Far better to rip it all out, replace with decent quality so you have a finished job that will look great for the next 20+ years.
If the home was rented "with subfloor only" in the master bath, someone severely failed at their job. If the Tenant ruined/ripped out previous sheet vinyl, someone failed again, either with a poor quality installation (by you-know-who) or failing to inspect during occupancy and bounce a poor Tenant out.
It sounds like someone (Tenant? Handyperson? Former Tenant?) did a poor job of installing shelving. What was there when you bought it? Based on that, who should be responsible for the cost of repair or removal?
Repairing a "cracked door...needs a few nails"? What do the pics show? Is this a split edge from the door being kicked open damaging the latch area? Or simple de-lamination of the veneer? A bedroom door is pretty cheap to just replace unless you anticipate more poor quality Tenants.
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Cleaning and painting the stairs seems high, are they actually that dirty, or very old, and never painted?
Foundation- water coming in? This should have been a priority, water is your worst enemy! You need to determine positively where the intrusion is; what is needed to stop it? ANYTHING you do inside the basement is NOT solving the problem. Especially if the current plan is to apply $225 worth of caulking. Gutters and downspouts, proper slope away from the foundation, redirecting water flows during heavy rains, digging out the foundation and re-waterproofing the exterior of it, these need to be explored as most likely fixes.
$750 worth of drywall repairs PLUS $4800 to paint? How many BR/BA? Did you collect damages from outgoing Tenant? If not, why not? If it was that rough when they moved in, or if they damaged and did not pay, someone has failed you again. For that money, they better be properly priming, multiple coats of a great paint product, with proper sheen for the type of area being applied.
Personally, I don't do Blinds, and especially in a lower end unit. Good quality curtain rods, properly and securely mounted, let Tenants provide their own curtains. Cheap curtain rods fall down too easily, and Tenants always remount them improperly, damaging trim and sheetrock.
Doorstops...the springy ones get damaged easy and you constantly replace them; friction stops are very hard on hollow core doors. Magnetic stops, properly, and securely mounted, these last a very long time without damaging the door, including the fact they prevent doors from blowing shut when room pressure changes suddenly.
I would be very curious to know how 3 sets of hinges need to be changed. not something that typically "wears out". It may be the door jamb has been damaged from getting forced open repeatedly, and/or having partial, poor repairs done; or improper screws were used to mount the hinges at some point, easily pulling out or just not able to be secured adequately.
