Any deposits and pre-paid rents get them at closing or you will never see them.

The reason you want them to have renter's insurance (with you listed as additional interest and/or additional insured) is because you want to have someplace to go outside of your own insurance if they do serious damage in excess of what the deposit covers.

The TO cost is in the maintenance budget, I also have not added in deposits to the rental income.

I strongly recommend that Renter's Insurance with Landlord as Additionally Insured coverage be required of the tenant; it's inexpensive and it is there should the tenant damage your property so that repairs are made prior to departure and a security deposit battle.Hope this helps - and please look into lease preparation services in your community. 

You'll need cash for earnest money deposits, lender deposits, third party inspections, due diligence costs, etc before you see your first OPM dollar. 

So expensive a fix that the deposit may not cover it and unlikely you will recover that from the tenant later.

My brain is spinning thinking about splitting deposits, classifying properties, and creating custom reports, but if I can get it set up properly I can see it being a great option.

You are actually losing money by leaving it in a savings account.When you deposit your hard-earned money in a bank, you are simply lending it to the bank so that they can utilize it for their purposes until you require it.Of course, putting your money in the bank is also low risk — you can pretty much count on your money still being there no matter what happens in the market.

at @Ashish Acharya and @Lane Kawaoka :What happens in the final asset deposition if :- we have ST/long-term loss from stock investments ?

Think of 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.