Home inspector, property manager (some states require various licensing), admin at a realtor office, contractor / trade apprentice, landscaper, home painter, lender, wholesaler, or co host / arbitrage STRWorking at a Lowe's or Home Depot would be good too.

I wonder if many of you feel that the landscape of the RE community has changed over the years to be a lot more supportive and inviting for newbies?

I run a small plumbing business in SF and my wife runs a small landscaping business and it is already a lot of work!

Only thing I will add is if you rent by the room, you also have to factor in landscaping costs (mowing the grass) and ideally cleaning of common areas (eg weekly cleaning service).  

Go to Etsy and search for "rental property tracker," and you will find hundreds of nice spreadsheets to track 10-20 rentals, usually for under $10.Software has extremely helpful features like online payments, marketing syndication (click a button, and your property is advertised on multiple sites), electronic document review/signing, maintenance tracking, and owner reports.

In addition to the $2,500 the tenants pay a monthly pool maintenance fees, landscaping fee, and split the water bill with the other unit.The unit has now been listed at $2,300 and is still not rented.

You could also work with a few professionals like a surveyor, landscape architect and/or engineer to help. 

@Joshua SunThings that drive the ARV the most - roof, plumbing, flooring, paintThings that don’t drive ARV as much - windows, landscaping, driveway

Go to Etsy and search for "rental property tracker," and you will find hundreds of nice spreadsheets to track 10-20 rentals, usually for under $10.Software has extremely helpful features like online payments, marketing syndication (click a button, and your property is advertised on multiple sites), electronic document review/signing, maintenance tracking, and owner reports.

While HI has a lot of potential for appreciation consider the changing landscape with interest rates and people's ability to buy a house right now.Ultimately, let the numbers decide.