Niceaft makes a good point about getting your wife lessons. I went basically from zero sailing experience to the Mac 26 M and it does involve a challenging, and continuous, learning curve Beware, in my humble and relatively inexperienced opinion the MAC does heal quickly. I've had my Mac about 5 years now and my wife has never recovered from the first sailing experience. Here is a description I previously wrote about our first sail:
I am a beginner sailor, so I have little expertise, or experience to back up my opinions. The sum total of my prior sailing experience was once crewing on a small dingy (18 ft) at a reservoir in Indiana and once crewing for my son on a 37' Tayana when he lived in Hawaii. I really enjoyed it both times but also had other interest and never pursued sailing. I retired a couple of years ago and my wife and I decided to convert a rental property we had in the mountains to personal use. The mountain property is close to a mountain reservoir with many sailboats. The lake is 3-4 miles long , surrounded by beautiful mountains and the elevation is approximately 9000 ft. So without a lot of thought or research I purchased a sail boat. I read as much as I could about sailing and took a beginning ASA course on the same lake in a 24ft Catalina. This course provided 12 hours on the boat. My wife did not read or take any sailing lessons. With that background I will respond to your inquiries as best as I can.
1. Good first boat- The Macgregor is a good boat. Based on experience I am convinced if the ballast are full it will not capsize. However, it does heel quickly and to me the impact of the heeling is exaggerated somewhat by the relative high position of the cockpit off the water. If you are sailing in conditions that are reasonably stable (Hawaii or Indiana) it will be a fine first boat. However, in the mountains wind direction and velocity often dramatically change within minutes.
My first sail on the boat was with my oldest son (not my Hawaii son) who had not previously sailed. I had him controlling the jib. I showed him how the 3 jib sheets (ropes-2 to jib, one to furler) worked, talked a little about sail shape and dumping air out of the sail. I took the wheel and mainsheet. We went out and had a pleasant sail, but we had gusty winds and had the boat heel to 30 degrees. Was not unexpected based on my readings, I also had the Catalina at 30 degrees and all I can say is the Catalina felt a bit more secure...but than again I had very little experience to compare to. My second sail on the boat was with my wife and it was a disaster. Basically went out on the lake and had very little to no winds for about an hour. No problem we got to relax and enjoy the beautiful mountain vistas. But suddenly winds picked up and within 10 -15 minutes were gusting to 40-45 mph. Early in this process I told my wife to roll up the jib, but she could not get the furler line to roll up (later determine she had not released the starboard jib line, so she simply pulled the jib tight as a drum and it was backwinded). The boat is starting to heel 30-40 degrees, I figure we cannot turn windward because we are to close to shore and the jib is still deployed. I am busy dumping wind with the mainsheet and vigorously informing my wife that if we want to live we need to get the jib rolled up or released. My wife decides at this point the best course of action is to grab the safety lines and scream. I'm thinking I got to get the sails down, so I pull the main in to get get my hands on the reef line and start lowering a fully winded mainsail. I was using my hands to pull down the wind filled main while using my knees to control the wheel. Before I can get the main down we round out twice, the second time the boat actually moves laterally (to port side ) in the water before it rounds out. We heeled so much the water was slightly over the gunnels but never came in the cockpit, one rudder and the motor were out of the water. Finally I get some control over the boat and note that the jib line was not released before trying to roll up the jib on the furler. Boat's fault? Absolutely not!!! Boat just proved it could stay afloat no matter what you idiots do. Novice captain in a challenging environment. Late in the process I did keep looking for why the jib was stuck, but by this time my wife was hanging on the life line and blocking my line of vision to the starboard side jib cleat that had not been released. Just my ignorance and inexperience. After this experience my wife is hesitant to deploy the jib, and I am inexperienced enough that I have difficulty single handling everything. So we did a lot of sailing this summer using only the main sail.
So how does this relate to your question...well it depends... its a safe boat and a good first boat if both of you have some minimal knowledge of sailing and you are not in extreme sailing conditions unexpectedly. BTW, I have no difficulty motoring the boat into my slip or onto the trailer. Always had fins down when going into my slip, but even with them up still not any issues getting on the trailer.
First ...yes I am still married to the same person. I have tried to get my wife to take sailing lessons, even went to the good folks at BWY , and had Cheryl provide us a sail on one of the first Tattoo, but even she could not get her interested in taking the helm. We still sail, but my wife gets very excited whenever the winds get gusty and I let the heel get close to 15 degrees. I have tried as best I can to convince her that the boat is entirely capable and comfortable with more heel, but all to no avail. So I now often sail with a jib that is quickly furled and a main that is quickly reefed
when the winds kick up (still have got 15 degrees heel with only a reefed main deployed!!!). Best advice I have try, try, try, to convince her to take a sailing lesson prior to going out together...and never, never, never, say were going to die if we don't get that sail down!!!
Good luck.
Bob
. Those years on the Phantom gave me realtime training on how to react to wind conditions. Going from a 14' dinghy to 26' sailboat was a fun learning curve. 
