.- Tenant Accountability: Many programs have strict guidelines for tenants, and breaking those rules (e.g., property damage) could jeopardize their assistance, encouraging them to be responsible.- Inspections: Some programs require annual property inspections to ensure compliance with their standards, which can occasionally be demanding.- Damage Risk: As with any tenant, there’s potential for property damage.

Once I work with will even go to 90CLTV, but they lend on very strict asset classes.Another family office I work with lends debt based on SBLOC. 

Strictly advice to move forward in these ventures.Your attitude may be the best thing about your ability going forward. 

I know the founder and know that they've set out to build a platform that takes the best features of sites like Furnished Finder and Airbnb and leaves out the clunkiness and annoying policies and practices.

Policy is fine.

It would cost less, initially, if a person kept it as four units and either rented the property out less of the time or not at all and kept it strictly as a vacation property.Any thoughts are appreciated

But you want your policies to be fairly firm. 

If they are VERY professional, they will have their processes in writing as verification that policies are enforced equally and fairly by their entire staff.6.

I don't think you can purchase a policy for one tenant, but you can create a master policy for all your units.

This would be the safest approach but also, anyone that is worried or has extra strict oversight in their area could simply avoid anything alcohol related in their packages.