What biek to get for $5000

Okay, so Ive been riding for 14 years. Im 19 now and last year I had a bad wreck and had to sell my bike for the insurance deductible for surgery. I had to give up riding for a while and it killed me to do so.

Fast forward...

Then in May of this year my father passed away. He was the one that got me started in riding when I was 4. After he passed, a ton of memories about riding and the good times we had flooded back, and now I want to start riding again.

He left me a TRX250R 4wheeler and a Yamaha Serow trail-bike. Im going to sell those, and my guns and Ill probably have about $5500 by the end of August hopefully.

Ill have to spend about $500 for some new gear, so Ill hopefully have about $5000 for a new bike.

So heres my question. For that much, what should I look to get.

Im a fan of 2-strokes and their reliability, but 4-strokes have been growing on my because of the ease and power.
The main thing I want is reliability. So Im leaning towards a 250 2 stroke because it will be easier to maintain and probably less prone to mechanical breakdowns. But Im open to the idea of a 4-stroke.

Ive never had a 4-stroke before so Im not sure what to look for when searching for one. What should I keep an eye out for?

What bikes would you recommend I look for that would be about $5k?

Thanks