So what would be the best choice if you wanted to go analog and digital with the same radio, and is there such a thing?
Just make sure you fully understand that there are multiple digital modes used in amateur radio, and they are not compatible/interoperable. Once you buy into a digital mode, that's what you've got.
Before buying a digital capable radio, make sure that the system you are going to use to talk to your friend down south is capable of doing what you want.
As for what is "best", that depends on what you need, what your budget is, and what your level of technical skills are. There's a lot of options, so choose carefully.
Also, when comparing prices of radios, make sure you consider all the costs, including the costs of programming software, cables, replacement batteries, etc. Sometimes the radio is the cheap/easy part.