A couple of trades people may have issues.

My thought is develop your skill, especially if it something you enjoy. 

It's a broad question but curious about trade offs between both options.What would you do?

Depending on the circumstances of the seller and your skills as a negotiator, the number you finally agree on with the seller can vary quite a bit. 

Even with Section 8, tenant screening is a skill to master.

We share the “Jack of all trades” traits lol.

Handyman who’s a roofer by trade for 30+ years.

@Mike Cumbie  nope, two move ins this week, 95% of rent collected, buying two more props, ( already sold one before I even close )  and actually making more money as I am trading stocks for the 1st time in 30 years. 

If consumer confidence retreats and spending dwindles as a result, the economy does not have many other sources of growth to fall back on, which could precipitate a new recession as the factory sector remains in the doldrums after taking a hit during the trade conflict with China.

Some will get a property under contract without the skills or knowledge to complete the deal, which can really waste the time of the seller - or worse.