My thinking is that by renting to a residential care facility I can effectively utilize all the space, earn above market rent, and help provide a needed service, while avoiding tenant parking jams. 

Let brokerage grow, tenants pay down mortgage, and save up for another property organically (Cons - slow growth, waisting equity// Pros - low risk)2) Cash out the $300k brokerage account, pay off the townhouse, start cash-flowing $2,400/mo, and save up for new investment or 1031 into multi family(Cons - cap gains tax on cash out, high Oregon income tax penalty, hard to find deals being $2,400 monthly cash flow) // Pros- cash flow, increased leverage into large investment)3) Cash out $300k brokerage and put into separate Multi Fam property, hoping for $2,400/mo+ cash flow, keep townhouse rented as is (Cons - cap gains tax on cash out, not utilizing equity PROs - increase portfolio value, higher upside with value add or rent increase on new units?)

Utilizing a wrap he has a mortgage note as an asset to offset the mortgage he’s still responsible for on the property.  

Unless a different one would be better that you could suggest   If you are house hacking you can utilize 3-10% down. 20%+ is great to put down but not always possible.

In Chicago you request a CHA Burden sheet and that gross number minus utility allowance will be what you get in addition to making sure bedroom size is adequate.  

Many Airbnb guests will want common utilities unless it is in a remote are where you go as a sot to sleep while hiking the area. 

You're marking the equities to most recent returns, the reality is a real estate investment to live in is a guaranteed rate of return and serves utility. 

I've been thinking a lot about Florida and I believe it's a great state for future potential investments such as purchasing and renting out (utilizing the BRRRR Method Of Course).

Quote from @Jacob Sherman: you can utilize no income no doc construction loans . fund 50% of the land 100% of construction upto 65% ARV .

So by utilizing leverage you earned $200 more.