So work on pushing through the anxiety of talking to strangers, take an improv class or practice on friends and family.  

Dwolla.com will let you do recurring payments and only charges $.25 per transaction.

•providing you with monthly and annual financial reports, so you always know how your property is performing •tracking and invoicing tenants for CAM charges •maintaining and keeping your property in exceptional condition and undertake specific preventative maintenance processes•professionally marketing your property to minimize vacancies and maximize income via my numerous industry related affiliations and web presence •overseeing the leasing process (if requested) finding qualified, suitable tenants, and professionally managing every aspect of the landlord-tenant relationship •overseeing initial tenant improvement installation and/or renovations •collecting rent and late •ensuring that your property complies with federal, state and local laws and regulations •maintaining insurance policies for the property and coordinating the payment of all property expenses •responding to tenant requests in a prompt and professional manner •providing you with a successful advertising strategy that keeps your property rented •credit and background screening to insure your property is respected •cost reductions- your property will benefit from detailed expense reviews and wholesale pricing for re-occurring and non-recurring expenses.

There is nothing wrong with having the debt that you described unless it is causing you too much anxiety.

Memorized/recurring transactions can be a great thing.

How can you maintain a positive cashflow with all these recurring expenses that if you weren't investing out of state you could have fixed them yourself for free?

With today's online banking and with recurring payments so easy to set up these days, it shouldn't really be an issue anymore, anyway.

Still have to do craigslist manually though :(Buildium also replaces Quickbooks with a very decent bookkeeping system and fairly robust reporting capabilities.As far as the rent collection, the tenants can set it up be a one-time payment or to recur monthly, weekly, bi-weekly, etc.

How did you overcome the anxiety and finally get started?

My experience with real estate investing and anxiety reduction comes from putting numbers on things.