Gap funding is a lot harder to secure, especially without demonstrated experience.

If a tenant moves in on October 15th, they pay the security deposit and a FULL months rent.

You can deduct that from their security deposit, send to collections or sue them. 

I wondered if SF route might allow us to secure better terms at maybe a 4% interest rate for a few years on the funds not rolled into current $150k potentially assumable mortgage -- and in a few years we could roll into a traditional mortgage. 

Less than 1% of my tenants leave owing more than their security deposit will cover.Screen well.

Cross-Collateralization: If you have other properties with equity, you might be able to use those as collateral to secure better loan terms or additional funding.4. 

Took one booking, the tenants broke contract by bringing a pet (dog hair and a bone were left behind), and Landing was not exactly pleasant to deal with in recouping security for extra cleaning and damages (dog used the ceiling fan remote as a chew toy). 

How can I structure the contract or investor payout terms to ensure they feel secure and confident in receiving a solid ROI?

We embrace S8 applicants, but screen them just like any other applicant.Many have an entitlement mentality and try to leverage their S8 voucher by pretending to be helpless:1) A percentage won't apply because they expect a landlord to waive application fees for them.2) Many cry broke and expect a landlord NOT to charge them a security deposit.3) Many of those same S8 tenants trying to avoid paying a security deposit, won't make an effort to call the list of nonprofits we send them that will pay their security deposit if they apply.4) A lot of them try to avoid paying for utilities.

They may require you to manually enter your financial data and calculate your net worth.Customization: If your finances are complex, you may need an app that allows you to customize your asset and liability categories and other information to help you keep up with everything.Security: The net worth tracker you select must ensure your financial data is secure.