I'd like to get these initial expenses/costs entered into the system and manage bookkeeping from there.  

I'm looking to assist you in any and all things in regard to your RE business.Quick qualifications:- Licensed CPA in NY- 2 Years Experience @ Ernst & Young- 3 Years Experience in Property Management- Website Design- Master's Degree in Accounting from Binghamton University- Phenomenal Excel & Bookkeeping skillsWould absolutely love to meet up/hop on a call and get to know each other.

Example - you will do the bookkeeping at $20 per hour.

On the other hand, as a Canadian, there are additional overheads (read taxes, bookkeeping, etc.) that make opportunities that seem OK, very marginal when all the costs are included.

I'm looking into bookkeeping services and have been hearing about Bench.co.  

Also everything is in place already bookkeeper, attorney, funding, management and maintenance.

Payroll, bookkeeping, etc can mostly be done remotely.Here is a great list of questions to ask a potential accountant:http://www.biggerpockets.com/forums/51/topics/70447-questions-to-ask-a-cpaAlso check out the www.NAEA.org page in your search.

Why not off load that to your book keeper?

Then, when you do your books, or get audited it is much easier for your accountant and auditor to do the books and audits because they won't have to ponder over and sift through your personal accounting.It may cost a little more to have personal and business accounting and taxes, but one the most-critical reasons by businesses have been successful is because we have super simple and super accurate bookkeeping systems.

I would continue to hire him as a subcontractor because it's cheaper and will make your bookkeeping easier.