I'd go as far as to say you are a classical liberal, as far removed from what today's liberals (so called progressives) are.

Now I'm studying CRE finance, investment, and tax strategies aside from my full-time job to better equip myself with the essential financial literacy. 

If you're concerned about Liability then I recommend you research where the best places to establish an LLC to maximize your protection and also study how land trusts work.  

@Will Boller, in a quick click around on Interval International's website (https://www.intervalworld.com/web/my/home) a major exchange for timeshare properties, it seems like it is 50/50 from my small sample looking at properties in the northeast USA, with a handful allowing Sunday weekly check-ins too.Granted, this exchange is not an Airbnb, but it is all weekly stays in condos run, presumably, by large professional operators that have studied this business to maximize revenue.  

( Study the market you are in, the deals, the rents etc.)

Want to combine the results of 10 different medical studies and look for patterns?

Some studies say that people are approaching 40% of their gross for housing now in the US!

However your situation becomes a trickier case study since these properties first served as your primary residence which could provide additional benefits form a tax perspective not available to an owner of investment real estate and nobody has a crystal ball and knows the property with certainty will transition into an investment property. 

I am curious if the fees I am being presented are in line with market norms:lender app fee: $10,000Origination fee 1% ($20,000)Lender costs: shows a fixed amount at $10,000processing fee $895registration fee $10,000Title and escrow fees: $4,000 est.6.5% rate fixed at 10 yearsPrepayment Penalty: Yield Maintenance months 1-114 (1% minimum)Third Party ReportsApppraisal Required Engineering Required Environmental N/A Seismic Report N/A Market Study N/A Funded EscrowsReal Estate Taxes Required Prop/Liability Insurance Required Special Assessments N/A Ground Lease N/A Replacement Reserves N/A Required Repairs TBD Debt Service Reserve N/AWould love to hear your thoughts on this as well as what you think is appropriate fees for the freddie mac sbl program. 

Here is my expected cost:Land: $475kAcquisition Costs (Environmental, Survey, Geotech, Traffic Study): $25kSoft Costs (Engineering, architect, impact fees, permit, legal, closing costs, taxes, interim interest): $300kSite Development Costs: (Earthwork, underground utilities, curb cuts, fencing, stormwater, paving, landscaping): $800k ($400k/acre)Subtotal before vertical costs: $1,600,000 ($80/SF).