My mind has shifted and while journaling every morning, that worry about school would always pop up as my “what’s bothering me” and why am I doing this without any purpose?

Both the AICPA and the Journal of Accountancy recommend cost segregation studies. 

There's a saying in journalism: "If it bleeds, it leads."

@Eric Merhar - Looking forward to seeing this journal as you go through the process!

Advise your tenant to keep a written journal, with dates, times and 'infractions'. 

It doubles as a journal for me and makes me feel like I have structure and control over my day.

I have been trying to do it "right" and use accrual, but thinking I may be making things harder than they need to be.Even with just a handful of properties, things are quickly spinning out of control with journal entries for accruing property taxes monthly (paid at the end of the year) and insurance (usually pre-paid and then expensed out monthly, but each property seems to be a little bit different).

I also owned storage and again l liked that.However I found new construction 7 years ago and last year was the 24th largest builder in Portland metro area you can look at the Portland business journal and see my name in lights.. 

If you've  ever driven through Springfield Wisconsin and saw the 1870's brick Church , I converted that into a house for my Sister - it was featured in the Milwaukee Journal. 

I find it refreshing, just like some people enjoy journaling.