Easiest was is to hire a bookkeeper. 

If cost is really tight, you could try and hire a bookkeeper, and take your end of year P/L to H&R Block.

I am curious what folks suggest I use for bookkeeping.  

HelloI am looking for a CPA firm familar with Commercial real estate who I can work with to support bookkeeping/accounting/tax filing / and strategies for Wisconsin.

It's a lot of work for our bookkeeper, accountant and controller but it's worth it.

We recently switched book keeping software and with that our website platform.

This make the bookkeeping and accounting more complicated.I am torn, should I keep this extra safe but more complicated set up, OR should I stick to just one LLC to hold and manage the property for simplicity sake. 

He’s super old school and likes to book keep everything- any suggestions on landlord/property book keeping books for investment properties?

Or is this a bookkeeping issue since you want it all automated through your software?

In your LLC’s book, you have to record this as distribution that decreases your capital account. ( I know you are good at Bookkeeping per your another post :) ) Also, remember, the interest in the HELOC proceed that was used to buy rental property can also be deducted in your schedule E.