Hi Rich,
It depends on your "health reasons". If not physically debilitating, whereby you have trouble performing normal everyday activities, then by all means you can have success with HF operating (I see you're an Extra class). Apparently you're looking to buy a home, and not moving to a nursing home or your daughter's house. I wouldn't let anyone suggest you put one foot in the grave

.
Others here have made good, logical suggestions on what/where to look for and I'm not familiar with the Chicago area, so I won't go into those. But you don't have to climb towers, roofs, trees, attics, or trench transmission lines, and still have workable antenna solutions. I'm in my late 70's, in remission from a lethal cancer, even live in an HOA with antenna restrictions, and I enjoy all the trappings of HF operating without any of the above mentioned supposed physical antenna installation "requirements".
Easy install: ground-mounted HF vertical antenna. And it doesn't have to be 20+ feet tall. For the last 15 years, I've been using a ground-mounted motorized screwdriver antenna that covers 10-80 meters without the need for an antenna tuner. It's a total of maximum 10 feet tall, with 6 feet of it a whip. Staple some non-resonant radials into the ground and you can have good results. You can also install it on a tripod, still without your feet leaving the ground. See Tarheelantennas.com, or Scorpionantennas.com for all kinds of install ideas. Personally, I've worked over 290 countries, decent contest scores, and nice ragchews on SSB, CW, and RTTY. I don't do FT8, but you can do a lot on that mode also. I do generally run higher power, but have had great success with 100 watts also.
Good luck with your research, and hope you can have fun on the bands when you find something satisfactory!
73, Bob K7JQ