Even if you filter out pending/contingent sales and houses on the market less than 14 days, there are still >50 houses (not trailers) in that price range. And since they have been on the market for at least two weeks, they aren’t going to sell above asking price.
Yes, houses require maintenance/repairs. Even expensive houses require maintenance, in fact maintenance costs are generally higher in more expensive houses.
That’s just one of the tradeoffs of home ownership. You should be ready to replace pretty much everything in the house over the next ten years. If you don’t like performing maintenance or paying someone else to do it, you should rent.
Finally, $250K absolutely counts as “under $300K”.