Since I have met tenant on multiple occasions and given that I have her 2 months rent + SD money, and the current landlord integrity is somewhat in question as well I'm inclined to proceed with the lease.

I suspect his volunteering is partially motivated because I told him when he moved in at the beginning of this year that I'm inclined to reward excellent tenants with a rent rebate around the holidays (e.g. half off december's rent).

Usually when people start seeing all the benefits they are inclined to at the very least learn more!

In my experience a LL who does not raise rents is not inclined to be meticulous about maintenance.

I've definitely talked about this with my agent, and we're on the same page about how we'd have preferred things to go -- and neither one of us are very inclined to recommend the attorney office we are using currently, in any future transaction. 

If they've been clean for years and want to rent a trailer on an acre in the country, I'm more inclined to accept them.

We are more inclined to terminate the lease at the one-year end.  

If it's a lower-class property, I'm less inclined to replace something when it's fully functional.

Personally, I'm much more inclined to hire a professional bookkeeping firm where all the aforementioned issues are addressed and taken care of vis-a-vis software that most likely might not be able to make it past a couple trivial use cases

Some days I'm much more inclined to take a chance than others.