I have a couple of Shakespear 5225s. They work fine for my mostly near-shore boating. The longer the better, 8 feet being a good compromise.
The radio choice is a bit more complicated depending on your particular boating parameters, where you boat and how the radio will be used.
Without doubt, you should get a radio with DSC capability and program it. Some folks want AIS to help identify other vessels. There are a few levels of AIS so do your homework if you think AIS is desired. Some radios have internal GPS capability. That means that you don't have to wire or network it to your plotter to get your current location. When wired or equipped, the DSC signal for help will automatically include your coordinates. I strongly suggest you get the internal GPS feature. The DSC will work without location data but the Coasr Guard won't know where you are from the DSC distress call.
If you mount your radio in a less than real easy to get to location (like tucked away in the overhead electronics box) depending on how easy or hard that is to use, you may want to select a radio with a multi function microphone that at a minimum allows the channel to be changed from the mike. Overhead or tucked away radios may also be hard to hear so a remote speaker may be needed. I think just about every radio these days have a jack for a speaker.
Depending on the size/length of your boat, you may want a hailer option that allows the radio to act as a paging system using a speaker horn that you would usually mount up front or on the top.
If you have a speaker -hailer opt, you may want the horn feature that can be set to sound the appropriate fog signals.
The ICOM 330 is a decent basic radio, but it needs to be wired to your plotter for location data. That radio is about $150. The ICOM330G has the same features but includes builtin GPS. That runs about $200. Add basic AIS and hailer, you will be in the $300 range. It may be that all you need is a decent basic model with DSC.
If possible play with some different makes at the marine store to see how intuitive it is to make the changes or select the options that you need most often. No mater how many seasons I have a radio, there are some things I just have trouble remembering how to do. That is especially true on my handheld.
For example, I use dual scan almost all the time but there are areasthat I boat where tri-scan is helpful. On some of may radios (maybe all!) I often have a hard time figuring out how to add/delete the channels.
Personally for me, the more function buttons, the better as opposed to having to navigate down multi-level function trees.