We will handle all the day to day activities management, bookkeeping, remodeling, repairs and etc. 

Does anyone have any recommendations on the best bookkeeping strategy or service.  

I'm wondering how BP members feel about outsourcing their bookkeeping to a virtual bookkeeper.

Complete and honest bookkeeping.

Try to start looking at the situation more like an accountant or bookkeeper would look at.

Some like Avail, TenantCloud, or TurboTenant are good all-rounders, but some are paid solutions and charge additional for accounting and other value-add features.Stessa is easy to use for the bookkeeping bit, but is a bit less developed for managing leases, collecting rent, screening applicants, etc.Azibo is building an all-in-one solution, free of charge, but the maintenance tracking features are still incoming.

I would like to easily, and at times remotely keep track of money in or out to provide to our bookkeeper.

My wife has been an RE professional for quite a few years (she manages manages almost all our units and does the book keeping and most years we have at least one rehab to manage) now so that if we have a negative year, we benefit immediately (versus banking the loss against future gains).$1M umbrella coverage likely suffices even with San Diego RE prices. 

Not all of that was RE training, some was bookkeeping, entity structuring, Anthony Robbins, etc.Not sure I'd do it exactly that way now, I was learning 14 years ago so not nearly as much was available for free online.

I made the leap to Quickbooks and hired a bookkeeper to get my business more organized financially.