I've had 8 Buells and 4 HDs over the years and had a great time on all of them. For me, half the fun was the bang for the buck when pepping-them-up. It's getting more difficult and expensive to that anymore and honestly, there isn't that need any more either. The power is up and they just work. People knock HD because they're generally slow and handle slow as well. But for what they are designed to do, they're hard to beat. And for anyone that's tired of working on stuff themselves anymore, you can't swing a cat without hitting a HD dealership or independent shop, plus their techs generally have H-D training certifications and are more capable than the ones that have to service the overly-complicated and overly-techy Euro brands. Add to the fact the HD dealers only work on HDs, other shops tend to be multi-brand, sometimes 10 or more brands and types of vehicles, which is why they don't have experts. BMW comes close, like the one in the Woodlands where they only have 2 other brands, Royal Enfield and Indian, neither of which require a degree in computer science. So, they have some master certified techs there. Yet, HD only ever sells HD and the aftermarket is the biggest in the world.
Can't help you on picking something that's limited to $9999 though. Whatever you look at, it should be different than the V85TT in style and use so you don't feel like you own 2 of the same thing.
As a Guzzi V85TT owner as well, I have to admit I love the bike. I can count on one hand the number of times I did not ride it to work over the last 28 months. But make no mistake, no one in Texas is capable of fixing the problems it has and the dealers for it, AF1 and Wild West, simply don't want to try because they don't know how. Their attitude shows it too. They simply don't care and you can't pay them enough to care either. Which is why I'll be trading it in on a new GS soon despite how much fun the V85TT is to ride.