I started out retail and eventually started dealing with collectors. I think that's pretty common.
If you get the right retailer I think it can make sense. If you get the wrong collector, you can also be up the creek.
I payed $2500 retail for a very nice TAF maybe 5 years ago and $3500 for IJ about 4 years ago. Maybe a bit high at that time for both titles, but I have not had major issues with either machine and neither one needed much to get them tuned into top shape.
I just bought a routed and unshopped FT for $1700 from a retailer, but I knew what I was getting. The cabinet has fade but the playfield is fully covered in Mylar and has zero wear.
I tend to have a bit more trust when buying sight unseen from a brick and mortar retailer.

I think it's at least fair to say that, like collectors, not all dealers are creates equal.
I've dealt with some I'd like to forget, and others that were genuinely nice guys trying to make a living. The good ones offered honest appraisals of what they were selling and plenty of support if anything ever went wrong. For those of us without a wide range of local collectors to deal with, or a wide selection of pins in general, finding a good dealer is sometimes the only option.