I debated about whether to respond, I’ll be brief

I sit on the other side of the coin. In a house that is falling apart, (not saying yours is) and a landlord who is just SURE that it is all my fault. He hasn’t done a thing to this place unless he has been compelled to…examples include:

the 20 year old furnace that went out (somehow that’s my fault)

the last time this place was tented for termites was 40 years ago, but somehow the fact there are termites here is my fault.
the termites ate through the fascia boards, and the fact that he has painted over them multiple times but now the city wants him to replace them is all my fault

the dishwasher which was broken when we moved in, he replaced. it’s a cheap piece of garbage, and what a surprise, within two years the timing board broke, somehow that’s my fault too.

many of the pipes and fixtures have rusted away and somehow since they’ve completely rusted through while we’ve been living here, that’s something I caused

You get the point.

IMO – you should put an end to him being a handyman who fixes thing while he is your tenant

It blurs the line between your business relationship. It may be that he is totally honest and forthright and all of these issues just fell under Murphy’s umbrella. It could also be that he sees ways to get around paying rent by “fixing up” your property, although that isn’t the arrangement you were looking for.

Find yourself a local and reputable service company (check homeadvisor or angies list for reviewed companies!) and tell your tenant that while you appreciate his help, you are now in a contract with a company and need all repairs to go through them. Be clear: no deductions will be made to his rent for anything (put this in writing) unless YOU pre-approve it. You didn’t hire him as a handyman, you are his landlord and expect to make your fair profit for renting the home to him.

If the issues and un-approved deductions suddenly disappear, then you might consider the odds in favor of him being a not so honest tenant and give him that “out” to leave when you find a suitable replacement.

Above all else – stay positive! It’ll work out. Your tenant odds of good ones 2 out of 3 is not bad at all ?