Each room will have a separate lease on it with a separate deposit following normal property management practices, and like you said, the leases have different start dates. 

., discounted first month, lower security deposit)•Pivot to Mid-Term Rentals (traveling professionals, snowbirds, digital nomads)•List on Multiple Platforms (MLS, Facebook Marketplace, Furnished Finder for mid-term stays)6.

I have got the security deposit as well .Please see your post… It says nothing about being rented and asked if you should take down the listing. 

Big things is be realistic on timing and maybe provide a mover and or storage unit deposit as they may not be able to figure that part out on their own.

However, we just started STR property management and it would be very helpful/look more professional to have the ability to esign contracts, autogenerate payout statements, direct deposit payouts, ect.  

You Open Escrow, deposit your Earnest Money Deposit and your due diligence period starts (unless otherwise written into the contract). 

You'd need to show the income on your tax returns and/or have a lease and first month's rent/security deposit for the unit you were living in.

A deposit on that site is required to bid.

The vast majority of lawsuits against Landlords are for wrongful eviction, security deposit disputes, and Fair Housing Violations.

I would keep the deposit unless I am able to rebook the dates and then I would only make her pay the difference for any unbooked nights.