Question #1 - I like Quickbooks. Every property is a separate Class. Track Expenses by Class, Tenants are customers. My accountant gets reports at the end of the year and it's all quite painless.
#2 Some properties are in my name, some in my husbands name. One business checking account takes in the money and pays the bills. I have security deposits on some of my houses (I think we will transition to move in fees...) and those deposits are in a separate savings account.
#3 I would leave everything in one personal name or another, never both and not in a business name until/unless you have to. Going "commercial" has different rules. Loans can get more complicated, insurance gets more expensive, and in my case in IL, some things must be handled by an attorney once you go Commercial/LLC (like evictions).
#4 Bookeepers are a personal choice. If balancing a personal checkbook is something you are good at, doing your own Books for rental property isn't that much different. Most of my bills are mortgages, utilities, property management expenses, taxes. I probably spend 3 hours a week on books and I have 13 SFH + 1 11 unit. For me that's easy to handle but Books are what I've done for the last 20 years and I have 3 hours a week to spend on it.
