Normal wear and tear would be a few small nail holes for hanging artwork, a clock, etc.

Investment Info:

Single-family residence buy & hold investment.

Purchase price: $86,000

Cash invested: $2,500

After being done with Rich Dad, Poor Dad, several podcasts (including bigger pockets)...

You nailed it with the traveling work crews.

Twilight/Sunset ShotWhy it works: Creates emotion and sets the mood.How to nail it: Capture both ground-level and drone shots to showcase landscaping and lighting.Example: This listing2.

Hey @Jonathan Vinas, @JD Martin hit the nail on the head.You are better off looking in areas with no restrictions if you can.I will say that some of the restrictions might be able to manage.

Years go by and eventually Grandpa gets tired of fixing porches, nailing gutters and steam cleaning carpets that 'have a couple more years in them. 

That would minimize and maybe eliminate the need for a loan for those properties.

Anyways, I think @Caleb Brown hit the nail on the head.

Using a 1031 to upgrade to a two-family could help you reduce or eliminate the $1,000 out-of-pocket expense you’re paying now.Also, condos often come with HOA fees that limit cash flow, so be mindful of their impact.

Fix it.We eliminate as much landscaping as possible: we take out flower beds and most decorative features, ideally, lawn mowing is the only job tenants have to do, because we know that's all we can expect from most.