It should be just fine fir a starter steer. My only concern is if a track over wheel kit will perform well in wet mud. Not really horribly soft and deep mud just slick sloppy mud. One thing about the Island. Is getting equipment here is a cost in itself so once its here. I'm positive I'll be able to sell it fir as much or more than I'll have into it. A lot of folks rent the one in town. Always a waiting list. We'll see what happens. If it doesn't do the job I need it to? I'll get a bigger high track skid steer. If that means talking to the bank? It is what it is.
However, I've never been known to go into any serious project half a**! It takes money's to make money's. If one starts off with junk? Hes going to be working with junk until hes not. Down time is a fisherman or loggers worst enemy. Time is all about money in both industries. We shall see what happens. I've got a long way to go yet before I can even get started. STIHL need a couple different implements, track kit, dependable truck to tow the trailer, insurance and probably a few more things that will pop up when I least expect it. Putting a lot on the line here, but I wouldn't do it if I thought I'd fail. FAILURE IS NOT AN OPTION!!!
Cut safe, stay sharp, and be aware!
IDK KK, IDK......
I understand your impatience, but let me talk you out of it. You are admitting you might not be making a great choice. The OTT's are okay, but a compromise is all they really are. You will dread install and removals of OTT's, so you wont do them as often, and have a bad compromise. You will hate what they do to asphalt and concrete, will absolutely dig into asphalt, and scar concrete, in a second..... Plus wear when you traverse those hard surfaces. They are slippery as all can be on steel such as your trailer deck, so you gotta chain that down, compared to a Rubber track, I dont tie down in my dump trailer, it never moves an inch. Yes, they do work in mud, but dang they will create a mess everywhere.
Down time. You MUST have a spare tire mounted on a rim, a jack, and a sufficient impact gun ON THE TRAILER, at all times for the flat you're going to have- many times. And think about this- A rear tire, poked with a hinge splinter, with the OTT's on. You're a sailor, so you already know some curse words. Well. when this above scenario happens- you're going to be a multilingual Sailor with words no one else can understand., and using them ALL. It will take you an hour just to stop cussing about it before you get to work fixing it. You wont need a spare with a CTL.
I'll reiterate since you didn't really elaborate on your business model- What are you going to be doing? Light selective land clearing, firewood collecting and sales, maybe some grading work and fill jobs, driveways and ditch culverts. From the pictures of you and the War Wagon, the terrain you show us? You will reget the wheeled machine in a few hours. You ever see jackasses do wheelies with them? Well, you're going to be doing them when one front wheel hits a stump you dont see because you have a couple of sticks in a grapple, that you have held way down low, because of the uneven terrain (you gotta keep the load low). Heaven forbid you experience the "wheelbarrow", riding on just one rear wheel, because that don't end well. A wheeled machine will beat you to death in that environment you show us in pictures, like there was an overloaded dance floor of mexican jumping beans in your kidneys all day..... How tight are your Glutes? (not that I really want to know) but you will be gripping the seat with your ass all day trying to stay in the seat. Got 'Roids? You will develop one or more..... You will want to wear a helmet in that terrain. If you are flying about, you will be flying about in the cab, and smack your head against the ROP, true story.
Never once, not even for a minute, to your bestie or anyone else, do you loan it out. It wil come back broken or they break themselves. Number one cause of injury and death in the equipment rental business is Skid steers and land clearing or debris pick up acitivty. You will not rent your machine.
It says something that you have a rental yard on the island and their machine is always busy. Go get some of that business. You being proficient, the job can get done for only a little bit more than if they do it themselves witha rental, and they dont have to get dirty, they just need to realize what will take them two days (one to do the work, another to fix up all the stuff they "damaged" while they tried to DIY, and you do it in a half a day instead- money/time saved for them.
Wheelie skids are for asphalt and roadbuilding, moving dirt around yards and stockpiles, or loading yards, not offroad, and not forestry apps. Before CTL's, there were Loegerring OTT's, specifically to take these smaller more compact machines into the woods to do some work because they were smaller, but they didn't solve the problems of "tearing up" land that shouldn't have been torn up with dozers to do the same work. Hence- the CTL was born. If the OTT's were good enough, no one would need a CTL. AND, the CTL can do asphalt and loading yards in a noice flat setting too, just as well.
Sorry- mile longer post, but- you gotta keep searching- I prefer my ASV, I dont miss the bigger chassis or HP, but, you could do what you want with an RC 60- if you have too. RC 75 or 80. Just research there are some Cat years and Terex years that had electrical issues, but no worse than any manufacturer. They still brand the ASV in Canada as Posi Track. (the original Forestry Mulcher). Look around for a demo and pay up now, first, and do it only once. (You relay if the skiddy bopper dont work out you can sell it? Hows that? KK- "Yeah I dont like it because of its shortcomings, but YOU'LL love it." Buyer- "I dont think so, Jerry, Imma gonna lowball you"
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That's what ours was supposed to be until a local busybody with a grass field airport a couple of miles away got involved. Now ours is orange and white. Now it stands out like a pumpkin in a watermelon patch.
. I agree. Only thing better then a tracked skid loader is a tracked cat loader, or possibly a wheel loader with chains.both too big and out of most people's price range. 
Now you guys got me second guessing and getting cold feet! I was going to run to town today and do a wire transfer but now Im thinking I should hold out fir a high track skid steer! DANG IT!
