He reached out last night and we have an appointment this afternoon for a conference call with his new bookkeeper to review our account.

I need a suggestion here to handle maintenance and cleaningTURNO for automated cleaner payment and scheduling along with inventory trackingQuickbooks / Bookkeeper to keep my PM business in alignmentChase bank & trust accountI'd like a better method for managing linens (bulk order) and distribution.I'd love to compare property management / cohosting agreements with someone to share best practices. 

Had several challenges with their bookkeeping after I had to make an adjustment to one of my monthly payments.

@Jonathan Buelow My accountant and bookkeeper could care less about what I set my rents at.

I do have a hired manager, but he is overwhelmed with the 3-5 projects we have going at any given time, plus managing rental properties and overall bookkeeping help with my end of the business. 

Just because the costs might be in the furture does not warrant not budgeting for those known expensesThen there is the misc costs of asset protection, bookkeeping, unexpected utilities (such as between tenants (tenant turn over) or failure not attributable to the tenant such as slab leak).  

I wouldn't worry too much about it, if you have a competent CPA or bookkeeper they should be able to review your books and within minutes have a strong grasp on who gets a 1099 (spoiler alert, not every contractor gets one, I'll be annoyed if I get one since I'm structured as an S corporation) and the amounts to report.1099 filings are usually a loss leader for us, so if you're working with a professional make sure you take advantage of them filing everything for you.

My bookkeeping firm provides me with a steady active income, which allows me to keep doing deals, cover unexpected expenses, and navigate the occasional black swan event.

Should I just bite the bullet and hire a bookkeeper? 

Tax Benefits are also a result of time, good bookkeeping, and tax advisory.- Market Appreciation is the least predictable, but historically, where you will make the most money.