was to young to remember drive in thetere that i went too, once or twice.
might suggest posting a picture of your lots. and give approx acreage of the lots. this would give other folks ability to see what you are up against. and help you narrow down your choices.
3 sites for used and new equipment
TractorHouse.com | Used Tractors For Sale: John Deere, Case IH, New Holland, Kubota.
MachineryTrader.com | Backhoes for sale, skid steers, excavators, dozers.
craigslist: chicago jobs, apartments, personals, for sale, services, community, and events
craiglist = be careful if looks to go to be true most likely a scam. if ad is there one day and gone next, most likely folks flagged it for scam and it was removed. ((have personal been flagging some crud lately as on search for a vehicle))
box blade most likely wanted, mainly due to the scraficer teeth / rippers you can raise / lower. to help break up compacted rock areas. then come back and re-smooth things out.
a rear blade might be a good choice as well.
land plane / scraper grader might be a good choice as well
all 3 above have there specific uses, but needing some sort of ripper/scrapper is going to be wanted most likely. to deal with hard compacted rock. a rear blade may seem extra, but there short thickness as in being able to back right up to an area and drop blade down to scrap rock away from fences to concrete wheel stops for cars and like. land plane / scrapper might be wanted as well. they act like a "sifter" per say, bring larger rock that has sunk down into the ground some and bring the rock back up on top of the surface. allowing the smaller stuff to fall down below.
TNT (top and tilt) it is expensive, but i am guessing you have enough curves, ditches, and like, were you wall want to constantly adjust the angle of the above 3 items. using the turnbuckles to adjust the 3pt hitch is slow and painful. the TNT replaces the turn buckles on the 3pt hitch with a hydraulic cylinder one for top link and one of the side link turnbuckles. it can really help ya get final touches on stuff and feather things out as you finishing things out.
make sure you get the extra check chains / sway bars/chains for 3pt hitch. 3pt hitches are better designed for pulling stuff, when you go into a turn and not pickup an implement you can twist and damage the 3pt hitch, the chains/bars help keep things under control better. also 3pt hitch not really best when backing up with implement on ground. while 3pt hitch can do it. you are at higher risk of buckling and bending the 3pt hitch up some.
FEL (front end loader) most likely going to be wanted, standard bucket with straight edge on it for a lip. so you can back grade and move material around as needed.
not sure if a "tooth bar" make it bolt on or strap on for FEL bucket. would be needed for you.
not sure if you would need a chain harrow or harrow or like, to help smooth stuff out. if you have pea gravel. and some grass / weeds here and there. then it might be suggested then. so you can rip stuff up with say a box blade rippers and smooth stuff out, then run harrow across stuff to drag all the clumps of dirt / weeds out to one side of the lot / spot to come back and shovel out / scrap away with FEL.
if you get option of a backhoe bucket, you do not need something largely wide, but say 6 to 8" wide, and longer between back of bucket to the teeth / cutting edge. hopefully some sort of hole/s on back side of bucket so if you get into wet mud, suction power does not hold the mud in the bucket (holes break suction and let mud fall out) teeth on backhoe bucket can be nice, to help break into really compacted nearly seems like concrete dirt. but it is just really compacted and dry dirt.
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be careful if drive in is old lot, and rock lot is worn down, you may be at higher risk, of snagging a wire or like going to individual speaker locations to each car spot. get your lots marked out for were all the wires run. and then take some video and lots of pictures. so you can review them a year from now, and remember were the wires are.
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to note it, if i see a lot of physical individual park spots, with clearly defined spots. i might suggest going with a skid steer. simple to the fact you can turn them on a dime in any direction. and ability to maneuver right were you want nice and fast. vs a tractor that has a big turning radius.
i am not a fan of smaller tractors in sub compact range, due to they tend to lack one crucial thing i require. "split" left and right rear brakes. so i can brake the right tire to turn quicker, or left brake to turn left quicker. along with simply getting my rear unstuck (been there done that way to many times).
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if you see a water tank couple hundered gallons or so. or a little trailer you could load up with some 55 gallon drums and plumb them together. to create a DIY spray rig might be suggested, if you are having problems with "dust storms" from wind blowing. so you can load up trailer with water and run across area to wet stuff down. every now and then you can pickup say a 400 to 500 gallon water tank that fits in back of pickup trucks fairly cheap. having stuff slightly wet after you get done grading, can help get stuff to "compact better" so folks are not tearing stuff up later on.
i would avoid the thought of hooking a regular trail to back of tractor. the 3pt hitch. raises up be default, and can cause the rear tires of tractor to come off ground. granted many folks including myself hook up trailers to 3pt hitch, but you need "STAY STRAPS/BARS" for the 3pt hitch so as to keep the 3pt hitch at certain position. between times of unhooking another implement, putting on stay straps, and hooking up to trailer. you could of hooked up to a regular truck and already spraying.
with above said, another sub compact tractor issue, you may not have a spot / hole that comes out under tractor just below the PTO shaft to put a ball on. to hook up to a trailer. so can avoid 3pt hitch all together when hooking up to a trailer.
a bigger lawn roller, or being able to load the FEL up with something, and put weight on rear end of tractor. and simply driving over entire lot, 1 tire width at a time, might help with compaction as well.