Boiling down your post, you are asking the following question: "Why do so many GPs want to raise capital in $25K - $250K (sometimes up to $1M+) increments from 'unsophisticated accredited investors' instead of from institutions?"

It puts this property considerably above the top of the market, would that really make sense for a rental property? 

The majority of our STR investors and vacation rental buyer clients ask or elect to close their acquisition in an LLC. 

If you're able to, start networking at local Milwaukee real estate meetups---this is the very best education and inspiration that you will ever find--I started real estate by signing up for a guru program but by far, my best education came from speaking to other active local investors who are actually doing deals or have built financial freedom---the nationwide guru program only taught about flips and rentals but there are so many different strategies that locals have and are successfully doing.

I am a real estate agent in South Florida that specializes in short term rentals 😊 would be happy to set up a call with you and chat! 

I have found that each time I've been about to purchase a property it "tells me" if it's a flip or a rental.

Don,Further I will say that investors only equate cash flow to rental income and they are unaware of cash flow through notes and other debt obligations. now granted owning the asset also gives you tax bene's that notes do not.

Can you do two rental properties with the 400,000 in your market?

I like using the same mortgage broker lender who is investor friendly, a lot of the little banks don't know how to handle rental income and you get issues with underwriting mid deal.

This may have changed over the years, and I had already had about 6-7 yrs of a small single family rental portfolio under my belt, and W2 experience in commercial real estate.