Would it be a bookkeeping nightmare to try roll both of these retirement accounts into one SDIRA to purchase a property of about $170,000?

This creates a high degree of simplicity from a bookkeeping perspective. 

Let's say, it costs you 1.5K to get your structures in place (holding LLC or Series-LLC, with or without land trusts, with or without separate operations LLC) and 0.5K per year (for maintaining the LLC properly, bookkeeping, lawyer and CPA, etc.) for a total of 2K.

And poor bookkeeping makes it a distressed sale.

Attorney can help you with the legal side of things, but your original post is about the clunky and overwhelming of the bookkeeping side of things.

This is my first house/rental, and I have no bookkeeping experience.

2) I can’t afford an accountant right now and have very little to no bookkeeping experience, so I was thinking about purchasing Dr.

If not, I'd be willing to help an experienced investor do some book keeping or other errands in exchange for letting me be by their side for some deals that they close just so I get some experience with buying properties.

Looks like your missing water/trash, bookkeeping and some electric (basement and hallways).

(Turned out to be a book keeping error) In hindsight I was EXACTLY what I needed.