There is no cookie cutter answer.  It is going to depend on what you want to do, where you want to do it, and what you want to do it with.  If you want to talk every time over 30 miles mobile to mobile with trees and hills and hollers then they are 100% correct. 

behind the door in Dad's office.  They were for the most part working when we went business band in 1975 with Standard C890L's

I have box full of them in the shop someplace.  They were mostly working 5 years ago when we began our first steps in converting to narrow band FM.  I'm showing you that to tell you this:  As long as you use a bit of care: don't try talking when the antenna is broken, don't wrap the mic cord up in the steering wheel, don't spill Pepsi on them, 2 way radios are pretty reliable.  Generally they are still working when you upgrade your technology.

Radio dealers like to sell systems and repeater time.  It is a revenue stream.  If what they are selling is what you need that is fine.  But most farms do no need to be able to talk mobile to mobile that far.  I forget if our base antenna is 60 to the bottom or the top.  But it allows us to talk pretty reliably base to mobile for a 25 mile radius.  Mobile to mobile 5 miles is our limit reliably.  Off and on we can talk 25 miles mobile to mobile, but don't count on it.

Your own repeater is not free.  It is out there exposed to every lightning storm that rolls through and will eventually go boom.  You just have to run the numbers and see how comfortable you are with the risk.

I like Kenwood and Icom.  I have a great local dealer to work with.

I don't know where you are located, but I did a dealer search based on your map dot.  You might talk to these folks:

Motorola makes good equipment.  My beef is the dealers seem to do what you mentioned and push time on their systems.  Also, they push high powered radios and little antennas.  I prefer a smaller radio and a bigger antenna.