I know I can hire a Cpa or book keeper to help me out, but I don't know if that will be the right decision until tax season rolls around.

I am at 29 doors self managed on Cozy right now here in the Chicago area, and other than book keeping I can't think of anything else I would want it to do. 

You now have less likelihood of a tenant trying to sue you for your personal assets, bookkeeping is cleaner at tax time, and you have a business foundation that you can build over time including credit for the business, additional accounts for CapEx/Vacancies, etc.TLDR: Use a business to do business. 

It does take a leap of faith that is done with the backing of solid analysis and knowledgeable members on your team to fulfill tasks you're either uncomfortable overseeing (like acquisitions, bookkeeping, etc) OR who can be consulted just for advice. 

I am a small company (me, plus a VA and a bookkeeper), but I think it's important to have it to keep things consistent, and from a liability standpoint.  

I suggest to use the 2% rule - your cost to setup asset protection and maintain it (you'll have initial costs and then additional overhead because of it, in a rough proportion on 75%/25% - e.g. let's say it costs you 3K to get the LLC structures in place, you should count an additional 1K annually in bookkeeping, CPA and lawyer costs to maintain it) should be less than 2% of your equity to protect (and again, using the 4K costs, that means you should have at least 200K in equity).

Hey guys, Im looking for a relatively cheap or free bookkeeping software. 

However the cleaner has to cover their transportation time and costs, pay their SS tax, pay income tax, pay for or do their bookkeeping, pay for cleaning supplies and equipment.  

@Billy Linn it’s receipts, book keeping, basic budgeting.

As you scale, consider hiring a bookkeeper if accounting isn't your thing.digb is a great software for this.