When we charter we are looking for only a few things. We are two couples who travel together every year.

One of us requires AC even on a mooring ball, so genset/ac is required.

The second thing we look at is price. We'd rather charter an older boat that meets our needs and use the savings for marinas and dinners.

The next thing we look for is how well the boat is set up for single-handling or at least short-handling. Yes, I can sometimes get the others involved, but mostly they prefer to watch.

A good chart plotter that's easily read at the helm and in sunlight is important. Good depth/wind indicators at the helm is important. Autopilot is really nice, but not a requirement. A bimini that allows me to see the main sail is very nice.

Working fuel/water/battery/etc. gauges are important to us. We once had a boat where the fuel gauges didn't work - drove us crazy not knowing how much fuel we had.

We carry our own BT speakers, so sound system is not important. We also use our phones as hot spots, so wifi is not important. Water is easy to get in the BVIs and not that expensive in our minds, so a water maker is also not important.

Cushions, both inside and out, are very important and preferable lighter in color. Realizing that these are easier to stain, we prefer the lighter color because it feels more open.

If two comparable boats is size have these items and the older boat is $750 or more less than the new boat we'd go with the older boat. If the price of the newer boat is only $500 more, then when we calculate the price ($500/# of people/# of days), it's not enough difference for us.

Coffee maker, blender, grill with propane are all very nice.

I'm sure there are other things, but this is our starting point.