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.
I have tried several and I would not go any less than the Warn or Ramsey 8000, just for the fact that YES the smaller one will work but SLOW and they get really warm when laboring. now I have an 8000 and fast and work great, You can even drag a vehicle on the trailer with all 4 tires flat.
The 1st kind of sex is called: Smurf Sex. * This kind of sex happens when you first meet someone and you both have sex until you are Blue in the face.
The 2nd kind of sex is called: Kitchen Sex. * This is when you have been with your partner for a short time and you are so needy you will have...