Buy in often and routinely.

Hot tubs are routinely maintained and covered by STR coverage.Fire pits if properly maintained are also pretty safe.

I'm interested in alternative investing opportunities (properties that don't involve rentals or routine fix/flip) to provide passive income and increased net worth. 

If you're going the umbrella insurance route, make sure it will cover you for several things including just the routine slip and fall (like mold or earthquake).

While certain routine tasks can be automated, you absolutely have to have your thumb on the pulse of your marketing. 

We routinely send critical notices, including renewals, terminations, inspections, past due rent, and others via Certified Mail, Return Receipt Requested, and additionally by Regular Mail.

Your goal of creating an income stream for a retirement beyond the 9-5 routine and enabling travel is both exciting and achievable.This community is here to support you on your learning journey towards making informed and wise real estate investments.

Doesn't bother me either as we keep our cabin highly maintained and routinely make upgrades.

I have a friend who does it with his and they routinely bump the rents to match the comps he provides them. 

Often the percentage will lower if you have multiple properties, so ask them if that's the case if you are thinking of doing more investing in this area- Maintenance costs | ask for an hourly rate for general maintenance, any routine maintenance that you should be aware of, and if they have an in-house maintenance team or if they use third party maintenance.