If these seniors are what would be considered, "well off, or handicapped", you can definitely make a decent living, most likely just doing windows. I remember back in the early 80's there was a definite slowdown of business in the area of the country where I lived. I had a stable job, which required that I spend time in an office setting a lot, and I remember when I first started at that job, I decided to wash the windows one day. We had several windows in the office, between offices and the aisles, plus a fairly large display window in the front of the store. By the time I got out the water, found some soap, some rags, a squeegee, handle, etc., and got them washed and dried, it had taken approximately an afternoon. (Lucky we weren't very busy that day). I certainly didn't enjoy doing the job and it took much longer than it should have. Time went on to the point where the windows were needing to be washed again and I was dreading going through that whole process when a young man, probably in his mid-thirties, came by the office, walked in and asked if we could use a window washer. I asked him how much and he said for a job this size, probably about $20. That sounded great to us so I decided to have him do the job. I went back to my work, figuring he'd come to me when he was finished, as I had already shown him where the water supply was. He had all his own tools, bucket, squeegee, rags, handles. I was barely back at my regular job in the office, when he came back to say he was done, would I care to inspect the work. I took a quick walk around with him and the windows were **** & span.............. in twenty minutes. I could hardly believe it. I paid him and he went on his way. Now that small office was in a small, one block long mall, where there were maybe 5 or 6 other stores, with large front windows. Within a couple of months he was doing all those other stores as well as ours, every two weeks. He said one time while he was at our office that it took him about 4 hours to do all those stores, but that a couple of them were quite a bit larger than ours. So, even if he charged each one $20, for 20 minute's work, that's $1/min. That's $60/an hour, x 4 hours = $240 for the afternoon. Not bad wages. As for the gutter cleaning end of the operation, there are some special tools that you can purchase that when attached to the end of a garden hose, will clean 98% of all the junk, gunk, dirt and live trees out of the gutters of most homes. Personally, if I were you, I'd limit that part of the business to single story homes. If you should have an accident with a ladder or just fall off the roof of a single story house, you stand a decent chance of not only surviving the fall, but doing so in good enough health to be able to continue on with your work. You would have to price those jobs out depending on the amount of time since the gutters were last cleaned and whatever else there were in the way of extenuating circumstances. It can be done, it just depends on how willing you are to work and work hard, and sometimes, long hours. Good luck.