I fly part-time for a group of four business owners that have two aircraft. Their newest toy is a beautiful PA31-350 Cheiftain. It has new paint , A/C (very necessary in South Florida), color radar, and a 430 color moving map GPS. The black sheep, now, is their older C-401 with one VHF radio and one VOR. Personally, I think the Cheiftain is an overpriced tank! I've tried to talk them into keeping the Cessna, and the biggest issue was the safety comfort and situational awareness that the Garmin 430 provides. My response " sell the Cheiftain, save the money and buy a Garmin 195 or 295 and mount it on the dash." They provide identical functions and features for 1/7th to 1/10th the cost!

I use a Pilot III for backup when I fly the "small planes". I like the display SIZE of the 195 better, but I like the OVERALL size of the Pilot III. It's a little bigger than a cell phone and fits nicely in a flight bag. The 295 is a boat anchor. My M/O is the same as what you propose; navigate with the old gear(ya gotta leave some of the challenge in the flying), and back yourself up with a handheld GPS unit. This leaves you clear of SUA's and MOA's and even the cheapest units provide a lot of valuable info beyond basic S.A. .
.....so I loaded up the plane and moved to Middle-EEEE..........OIL..that is......