Now to follow that up do I charge another Pet Deposit for the new year?

Here are some of the highlights: quickly set up bank accounts for each property and sub-accounts under those for things like security deposits and CapEx; virtual credit cards tied to each property; quick transfer of funds; ability to send money back and forth to tenants (some platforms are for collection only but won't let you send your refundable deposits back to your tenants); easily categorize every transaction into IRS Schedule E categories for reporting taxes; ability to split transactions; tenant management from vetting to drafting lease agreements to collecting rent.

Then I could keep his/her deposit money and any capital improvements put into the building.

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.

We charge a deposit on direct bookings to offset this risk. 2.

I'd have to double the security deposit, raise the rent by 20%, and double the cleaning fee to even make it worth considering-- which I would if people were willing to pay but the market doesn't support those prices.

Here in NYC you will get laughed at if you ask for a T12 on deals that go into hard deposit immediately. 

5) Is one month rent security deposit enough nowadays?

This is very odd especially if there was no deposit and work was performed .

My tenant, who received the company check, addressed to our company, was able to cash/deposit it at their big name bank.