In addition to organized bookkeeping, Buildium provided other benefits that accounting only softwares do not, such as lease renewals with esignatures, maintenance requests, a tenant portal for rent collection, 1099 preparation for vendors. 

NEW TENANT GIFTSHere's what we give new tenants.....Cleaning Bucket with Cleaning Supplies:white vinegar, baking soda, awesome degreaser, disinfectant wipes, carpet spot cleaner, magic eraser, all purpose cleaner, scrub sponge.Tote Bag with Useful Items and Tools:hand soap, paper towels, plastic garbage bags, toilet paper, toilet plunger, Zip-It (strip for clearing hair clogs from drains), plastic clothes hangers (6), shower curtain liner (good quality cloth one), laundry detergent, dish soap/dish detergent, cutting board, "Freeze the Grease, Save the Drain" kit, “Recycle” bag for collecting materials for recyling, magnet with our name and contact information, picture hangers.Refreshments In the Fridge (for move-in day): several bottles of water, healthy snacks, bottle of sparking cider with a welcome note attached.Larger items: Welcome mat, shoe tray.

It's important to note that some of these accumulated fees and charges that make up the payoff amount may not be collectible.  

I even do my own taxes on turbo tax, but use management software to collect rent and track expenses.

These are building improvements that likely won't impact your rent collection but you are still obligated to share in the costs.

Flip props, and collect the rent 

When our tenants move in, we collect the first month’s rent along with a one-time, non-refundable move-in fee that’s typically a little less than half of the monthly rent (for example, $600 for a $1300 rental).

you should collecte deposit the moment the lease is signed or 24hours max. no deposit, the lease is void.

One of my criteria for investing is not to buy in any area where I would not feel comfortable sending my wife to collect rent in the dark.  

As for the security deposit, it will depend on the title that it was collected under, security deposit or advanced rent.