Birdus: Where are you located? Is there a good club nearby that could use you as an instructor? And many have already asked, is this a full time career move or a side gig, or maybe a retirement job?
Financially, I cannot say what you should do, but I do know that I owned an SR20 for 10 years and finding an instructor back in 2009 who had any experience with the Avionics was difficult. I am sure it is easier now, but the point is the same: are there any pilots around you that need your services?
If you are in the DFW area: there is a Ce-120 in Rowlett that is offered for rent/training. There is a Flight School in Denton that has a couple Citabria available. And there are lots of RV pilots that need instructors. Heck, I have a Luscombe project in the works and will be looking for someone just like you to help me learn the little plane, meet insurance requirements, reintroduce me to tail wheel (it has been a long time - that endorsement should probably be stricken from my log book by now.)
I do know, good instructors seem scarce these days. I am hoping to get my Luscombe back in the air sooner rather than later - when I do, I'll need a tailwheel instructor, and I have two daughters and a wife that are lining up to take lessons too. Which I might add says a lot about Luscombes and planes like it, when there was a 177RG and later a SR20, everone was happy to sit back and watch the clouds, listen to the XM radio, etc. I acquired this project and suddenly, all the women in my life want to learn to fly. My oldest daughter explained it like this - the avionics in the SR20 were intimidating and that plane was meant to go places, but the stick and simple guages make the Luscombe look fun.
Only you can decide if becomeing a CFI fits your time constraints or financial needs - but I for one believe there is a market for a good Tailwheel CFI. Best of luck on whatever you decide.