I have a warn 2500 that I have used for over 5 years. It gets used a lot, probably loaded at least 200 different vehicles in that time, most of which didn't have air in at least one tire, some without an axle... or 2. I would consider it the minimum, if you know the vehicle is going to need it on occasion. I originally bought it for use with a 72 Bronco and related non-functioning parts vehicles. It would drag my bronco onto the trailer with all 4 tires flat, easily.
I would recommend staying away from the Walmart, Checker Auto and Harbor Freight versions that attach to a trailer hitch ball. I have seen several of them fail before the first rolling vehicle was loaded on a trailer.
50 ft cable is nice to have, to help keep several wraps on the spool to make cables last longer, and gives a little more reach into alleys or back yards. Mine has a small crimped loop that attaches with a 1/4" screw, and has failed both times (5500#+ Dodge truck) I did not leave 5-6 tight wraps on the spool...like you are supposed to.
Mine is not as fast as my brothers 8000# warn, but it is easier to control the speed when things get close to rubbing or scraping. A snatch block can be used to slow it down, and also increase capacity.
Mine is mounted to a plate with a receiver tube, so I can use it in any 2" trailer receiver, front or back of the vehicle, and store it locked away, out of sight. Makes it easy to chain to a post or other anchor away from the trailer also.
Buy a good quality, Warn, Ramsey, etc 2500 or better and you will be good to go for weekly use for several years.