the thing of it is, you now own a vehicle that is well over twenty years old. and at this point in its life, mileage really doesn't matter. while mechanical parts like starters and water pumps are not as likely to go south on a lower mileage(which is still probably north of 100k) truck. its the soft parts that will give you fits, like the hundreds of feet of vacuum tubing under the hood.
so while you do not have to do your own work, now or ever, it is in your best interest to start. for starters these cruisers are very simple, while a peek under its bonnet might lead you to believe otherwise. simple truth is they are carbureted engines that still use the basic triangle, fuel air spark. if it won't run, something is missing.
the sooner you start picking at it, that much quicker you will be pretty handy with it. if you do not know what certain parts do what and how each part interacts with the others, these will nickle and dime you to death. but when you know that an oil drip here and ticking noise there is not that big a deal, they are much less stressful to deal with.
when you do the work yourself, the cruiser will talk to you. you will learn that certain noises and feels will tell you when and what parts are beginning to go bad and how long you have till something "needs" fixed vs when something "should" be replaced. compared to having no skills and calling the tow truck while in the parking lot at work when the thing "just suddenly starts puking water everywhere, for no clear reason".
the other thing is, this area is not very cruiser rich, it's pretty poor actually. there are no shops anywhere around here that specialize in cruisers. you will not see very many other cruisers on the road. there are forum members scattered about the region however each pretty much being the only one or two in their towns or areas. and the cool thing about most cruiser owners, they like working on them as much or even more than actually driving them.
good luck and welcome the region.