I manage properties owned by two or more people.  On the last day of each month, I need to send out statements and checks to people based on their prorata interest in the property.
 

While the reporting is for the whole property, you can designate that the Owner checks can be split between two Owners, based on their percentage of ownership.

What is the software requirements for TenantFile?
 

The Tenant File is compatible for Windows 98, XP Home or Pro, 2000, and Vista.

Can you set up monthly reserves for individual properties and does it automatically calculate proportionate monthly payments to several owners of the same property?

You can set up a 'minimum balance' (reserve) so that before the Owners are paid (checks are created automatically), an amount is deducted to remain in the ledger.

How difficult would it be to begin using this TenantFile two or three months into the year?
 

As far as setting up, you will be pleasantly surprised - it's very  easy.

You only need to enter the Owner Name, Property Name, Unit Address, and Tenant Name to get started. You can enter 'starting balances' from last year, then automatically post any rent charges and receipts for the first 2 months.

Is support available?

The Tenant  File comes with 2 months of free phone support and free email support after that.

Are income, expense and cash flow statements available for each  owner each month?

We have student rentals and can have up to 5 or 6 tenants in a large unit who make separate payments for the rent. We do need to track payments by individual.  Can we do this with this software?

The Tenant and Rental Unit are actually part of the same info, so for each Rental Unit you can enter two tenant names and tax id numbers.

However, in the scenario you mentioned, since you have to track individual payments, you would set it up similar to a six-plex.

One property (or building) with 6 rental units. Each rental unit would have a separate rent (1/6th of the total) and each Tenant would be maintained as a separate renter.