We've never even had a tenant try to sue us over a security deposit dispute.For the last 10+ years, I have occasionally asked for just one example of an investor that was sued, lost, and the judgment exceeded their insurance coverage.

In addition to taking 6-9 months to close, they are also subject to (i) annual audits, (ii) annual REAC property inspections, (iii) recurring annual MIP payments on top of your interest rate, (iv) large initial deposits to the replacement reserve, (v) commercial space limitations to 15-20% EGI / 25% NRA, and (vi) less forgiving underwriting with 7.00% minimum vacancy rates when determining our underwritten NOI.

Consider all the things that could go wrong and see if the lease addresses them: unauthorized pets or tenants, early termination, security deposit, lease violations, late rent, eviction, lawn maintenance, parking, etc.5.

And all the folks that could never get a deal to close and lost their deposit to them and EM etc etc..

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. 

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.

I also require additional security deposit and sometimes a guarantor if they were approved in this manner.I also agree that this situation sounds like a pattern not a one-time mistake or short term tough situation that caused this.  

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

A deposit on that site is required to bid.

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.