I pilot a very different version of your bike: a '97 Buell S3 Thunderbolt.
The people who talk about high maintenance costs on a Harley, esp. the Evolution Sportster motors we both have, don't understand these bikes.
Yes, repair/maintenance costs at a Harley dealer are high - you'll hear the term "stealership". The good news: you don't need them.
The motor is stone-axe simple. It has pushrods and hydraulic valves - you won't ever have to adjust the valves, something that's a MAJOR pain in the rump on most other rides. A few of the newer Jap cruisers now do hydraulic valves too, but not many on the used market.
Doing the valve cover gaskets will be no problem at all. Get some ball-end hex keys in SAE and it's a snap.
Another huge advantage is that your transmission oil is a separate pool of goop than your motor oil, plus it's a dry-sump system. Jap rides generally do tranny and motor oil as the same pool, which long-term causes issues.
The 883 motor has more performance potential when modded than any other Sportster-based motor, mine included, if we're not talking about splitting the cases (read: custom crankcase/rods).
You have fairly small pistons that weigh less than those on a stock Harley 1200 (which is how mine came). I've upgraded to a 1250 with Axtell ceramic-lined barrels and forged race pistons. But because my crank is heavier than yours, I had to run heavier pistons than I could have if I'd started with an 883. You can buy kits to swap barrels and pistons to 1200 or beyond from an 883 starting point, with lighter 1200 pistons than normal (forged to boot instead of stock cast).
The reason I had to swap barrels/pistons (and I did serious heads as well while it was apart) was that when I bought mine used, the moron had installed a higher-flow air intake without re-jetting the carb. And then he didn't run it seriously. He had told me it WAS jetted right...not. So I melted a hole in the front piston doing 80mph. Sigh. Didn't hurt the bottom end any thank God. Once I had the new piston/barrel kits in hand it was about a three day job swapping it all across. The hard part was rigging a hoist so I could shake it upside down with the barrels and pistons off to get the loose piston bits out of the crank. Yeah, the whole bike...Buell motormounts are a freakshow, it was just easier than yanking the motor.
Anyways. My point is, Harleys are like Rugers: they respond well to amateur repairs and even modifications

. With 10.5:1 compression, Mikuni 42 carb, KT Engineering pipe and 2004-spec Buell heads with a stage 2 port, I'm pulling 0-60 in about three seconds

. Less than $2.5k with new parts would take your motor there

and could be done in stages as desired.