I played around with the software from 365villas and ultimately realized it was just complicating things instead of making them easier at least for now.I want software primarily to help with calendar syncing, rate syncing, rate optimization, inbox syncing, providing a good website template that can be white labeled, bookkeeping, and generating  property reports.

On the tax front, I do my own bookkeeping, but work with a local CPA (actually working with an EA - Enrolled Agent) firm to prepare my taxes.  

Biggest time savers are online payments, bookkeeping, owner payments, tenant portal and advertising.

Multiple LLCs require a bit more bookkeeping, but also provide segmented asset protection as @Bryan Otteson mentions, so there are many other points to consider.  

(I can, of course, provide my full resume and samples of my work at a later date if interested)I believe I can deliver the most value to an investor in a role which involves bookkeeping, financial analysis or creating content for investors/lenders.

I am a CPA and am comfortable with bookkeeping and filing to form an LLC. 

Each investors criteria is different but our guy is a PM, general contractor, has 24 hour handy man service, book keeping, etc.

However, being a newbie, I'm still stuck with the bookkeeping on your customer's side (i.e.

They are my retainer bookkeeper and tax preparer, pretty much it is a writeoff what goes out in the business card, so no argument there and more easier.

If you don't already, and with your experience I'm sure you have, you will be able to afford a FT bookkeeper should you choose.