I have had a 1998 Bobcat 873 and now 2006 S300 skid steer. Bought both machines used and with relatively low hours. S300 has AC/heat, 2 speed, hydraulic bobtach and radio. Also have a TC 5610. The skid steers are just more rugged machines. Don't have to worry about the mono boom or what your driving over with a skid steer. The boom is the weak link on the TC for construction work in my opinion. I have done a lot with the mono boom but I am always a little careful with the corners or the bucket when lifting or digging. Can see attachment or bucket better with skid steer. SS better in tightly confined areas and can lift higher. My 873 only had cab heat. I would not own a skid steer anymore without A/C.
TC will win in the comfort, speed traveling down road and easier in and out of cab. Can't easily or safely get in/out of cab on SS with lift in the air. Often I want to lift something and get out of cab. Can do with TC but not easy with skid steer. Driving a skid steer all day with foot and hand controls is definitely more tiring than a TC. I would opt for advanced had controls if I now had a choice. TC cab is quieter. TC has all around better visibility. The back of a skid steer and rear corner are nearly complete blind spots. TC much easier on turf than a skid steer. The TC will probably lift almost as much as an S205. I modifed my TC and am lifting probably close to 3000 lbs. Have not broken anything yet but really careful with heavy loads.
Unless I am doing tough tasks, such as heavy lifts, more digging or tight confinement, I still tend to opt for the TC. I still use a lot of 3 pt attachments on the TC. Can't do that with skid steer.
I have bucket teeth on both my TC and SS. The SS will dig better but mainly because of its more hp and weight. However, the TC will dig well because of the bigger lift and tilt cylinders I installed.
I am considering getting rid of the SS for a compact wheel loader. More lift, better visibility, can get in/out of cab with lift in air and can still use my SS attachments. Compact wheel loader may be a consideration for you. The major downsides are more expensive, weigh more, and not as good in tight areas.