If your goal is to buy a nice vacation home and enjoy some supplemental income I suppose you can do whatever you'd like, but STR investments carry plenty of extra risk and upkeep.

Most recently I've been using Crexi to help supplement my commercial searches.

The issue: my job, healthcare, is supplemental (no guaranteed hours.)

Although my specific situation is a bit different than most people as I am will be a retiring federal employee at 57 and will receive a social security supplement till age of 62. 

The good news is that some landlords that are older and were doing this as a “hobby” or supplemental retirement income may be looking to unload as recent times have been pretty stressful for some.

Although some people may do a supplemental loan for Cap X as well.2.)

It states that everything in the original lease agreement and supplemental forms stay the same unless specified otherwise in this renewal form. 

Do I need to add supplemental on top of my existing homeowners insurance because it’s an investment property?

The city of Ventura, Malibu, and calabasas (during a healthy market) can provide some additional supply that will supplement the lack in Thousand Oaks.

I have recently read Brandon's book " The Book on Rental Property Investing", which led me to have an interest in real estate investing as a possible additional way to build passive income that could supplement my profession in the future.