Trump has been using a personal 757 for quite a while now. Long before he first ran for President. I don’t think Boeing even makes them anymore because newer models have superseded it. I imagine he is quite comfortable with it.
If you already had a 757, would you kick it to the curb?
Not only has DJT owned a personal commercial size jet for many years, he also owned a commercial airline, Trump Shuttle, which operated flights between NY/Boston/D.C.
The 757-200 is about the same size as the 737 Max 10 (the older plane is about 12 feet shorter, and they have roughly the same passenger capacity and the Max 10 has a higher cargo capacity).
The last 757 left the assembly line in 1992. So none are younger than 20 years old.
Trump Force 1 just underwent a major Overhaul/Service/Interior upgrades and Painting a few months ago.