It is vital that you know what you're doing.

You need to develop healthy personal habits and work habits (I struggle with both).

@Jennifer H.A middle of the road tactic we frequently employ with our student tenants, if they drop the ball at the beginning of our relationship, is to strictly enforce the late fee - even on the first offence - but, once the late fee is paid, we tell the tenant if there are no further issues throughout the remainder of the lease we will either apply the late fee to their rent at renewal or refund it along with their security deposit.This keeps the relationship with those who honestly made a mistake and, for those who make such conduct a habit, it is - to borrow from @Jeff Rabinowitz - a drop in the liquid fund ;-)

If the two of them cant find a time for it to work - it either isn't important enough to the tenant to be there/have someone there or your relationship with said contractor isn't strong enough, meaning that all of the people I use will make it happen - after hours, weekends, etc.Furthermore - if the schedules just don't jive tell the tenant you can put a lock box on the property and/or give the contractor a key.I would highly recommend that you do not get in the habit of meeting contractors at your property as a chaperon every time something needs fixed.

In this business, acting ASAP is vital.

I was in the Navy, we had a 1 week money management class right after boot camp and another 1-2 hour training every year and it didn't make any difference. people's money habits are either ingrained while growing up as a child from their parents or relearned as an adult due to making bad decisions for several years.

Neither of which could be done safely of course.So, the municipality has no way of knowing whether a unit was returned to the landlord in a safe and sanitary and habitable condition, short of performing inspections after any change in occupants.

Thoroughly understand the target market, including their income and spending habits.

Old habits die hard.

Replace your unproductive habits with productive ones.