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https://www.facebook.com/marketplace/item/1739620979522240/?ref=browse_tab&referral_code=undefined
If you have a look at this sort of thing - not too expensive and will probably get back near what you spend in a year or two = you want 4 stroke with service history and an apparently sensible owner. Jacket and helmet very very important.
I reckon you could get started for around 1500, just don't buy a lemon.
Something like the ER6 covers most of your wish list. If you're tall it might not be the most comfortable though.
Everyone's right about the gear. I still have more money invested in riding gear than I do in m/bikes.
Some clothing bargains on eBay are incredible. A lot of people buy decent gear when they are old and flush then don't do anywhere near as much riding as they used to and eventually sell it when they sell the bike.
If I were starting again I'd probably look at Knox under armour and a Tucano Urbano all in one waterproof. Trousers are a bit harder because the best textile trousers are still money but Rukka stuff sometimes comes up that's old but not worn much. If you have an all in one suit it doesn't matter if the textiles not still fully waterproof.