Would you say this is a safe strategy for beginners since I am in a sense “getting my paint brush wet” and could use the additional support?

Would it be nice to buy stocks now at 20-30% off "retail" price with a few clicks rather than wielding a hammer and paint brush and/or chasing down contractors and unclogging toilets?

Next time I will budget the work conservatively without me lifting so much as a paint brush.

You won't have time to do that if you're busy slinging a paint brush. 

YouTube and knowledgeable friends were extremely helpful in troubleshooting and learning tips for the different jobs.And highly recommend this paint brush for trim and edgingWooster Q3211-2 Shortcut Angle Sash Paint Brush 

I use all the same paint for our units so I had the paint, brushes and equipment they needed.

That market might have already recovered or is still declining.I talk with many BP investors on the phone.One thing I get from every call is how different each state is with the local opportunities.You can't paint your individual investing goals with a broad paint brush that encompasses the whole nation.You have to drill down to local metrics.

I don't trust my tenants with a paintbrush, wrench, or hammer.

Do you buy the Mr Clean to clean the place, do you pay for the paint brush, gas/oil for mowings and maintenace on equipment?

If, like many houses, that crack has been there like forever and hasn't gotten any deeper/thicker than like an eighth of an inch, run down to your local home improvement store, buy a small container of wall patch, sand paper, a putty knife, some matching paint and a paintbrush.