Well an analogy to your argument might be the painting of an entire rental property exterior (not just the bad spots in need of it).

I barely graduated high school, yet I own 64 rental units and between that and a painting business I started 3 years ago I will never have to have a job again.

All apartments have carpet/ vinylStandard paint

And he likes to barter dental work for other services (house painting, roof fixing, tree trimming, etc). 

I will do the painting, windows and kitchen/bath installation.

It is going to be a house hack as im utilizing my VA loan entitlement so it is costing me (almost) nothing out of pocket (obviously needs some paint and minor updating, it was built in the 70s).

The first floor kitchen and bathroom has been upgraded and I plan to add some fresh paint etc when the current tenants lease expire.

It is mostly rent-ready (will paint a couple of rooms), and I will hire out the property management.Here are the details:Anticipated Purchase Price: $64,000Market Rate of Comps: $85,000Anticipated Monthly Rent: $950 ($11,400 annually)Total Annual Expenses: $9070P&I: $3177Insurance: $300Repairs: $1000Taxes: $1769Property Management: $1140CapEx: $1000Vacancy (6%):  $684Net Annual Cashflow: $2330 ($194/mo)I see this as a nice balance b/t cash flow and potential appreciation.  

But all of that's very different than carpet getting thrashed, shoving who-knows-what down a garbage disposal, have to do more paint touch-up after a 12-month lease than living in your home for 5 years, etc.

Minor, mostly cosmetic stuff, maybe appliances, paint, carpet, hardware, light fixtures.