So, from time to time we get contacted by someone, that’s probably bought one or two properties in their entire life. 

You run the risk of the IRS classifying the property as 'personal use' if you rent the property for a lot less than FMV.

For BRRRR investors, seasoning requirements can significantly impact your ability to quickly recycle your capital.While most lenders require you to hold the loan for at least 6 months (aka "seasoning"),Fabulous 5BUY - short-term bridge financing to help you with investment property acquisition.REHAB - With up to 100% rehab financing, you can stay liquid through renovations.RENT - Tenant in place or future tenant.

Let them work with you on your ARVs when you get serious about a property (don't thow them a thousand deals you see and expect them to do CMAs all day long...make it worth their while).

Based on your question I would also advise you to seriously consider using a property manager.

@Nam Pham  Assume likely an older property on a pier and beam foundation, as compared to a slab foundation?

I, like you, have a handful of my own STR properties that I self manage, and manage just shy of 20 STR properties located in Bryan / College Station, Tx for out of state/country investors. 

I'm unsure what the right path is, but I've been reading about investing in owner-occupied, multi-family properties.

Been hearing a lot of investors had their properties royally screwed up from Milton.

I'm in discussions to buy a second home/investment property in Vermont.