Most new construction deals require you to give up to a 10-year warranty on some items while most fix and flips come with very little extended liability after the sale excluding gross negligence which is not stopped by an LLC in any case.

With that being said, in a worst case scenario, you can always hire a property management company to handle the day to day items if it comes to that. 

I would try to buy properties starting at a specific date so not large ticket items come up.

You're giving up some good tax benefits since you're in the tier of taking itemized deductions.

I will always look at the air handler and make sure tenants are installing fresh filters (most neglect this item).  

They won't learn those items until they actually do deals. 

Are these the only items we need to document?

A savings to put deposits and another account for everything elseyou don't need separate bank accounts as accounting software will classify all of those items.

Once I get to a point that it is making enough per month that I feel comfortable taking money out of the business that would be when I get to the point that it is worth have a specialist assist me in all deductions, credits, and future items that will help me to transfer from a W2 to working for myself fully.

In my area (near the beach) its mostly families and they want cabanas, baby items, chairs, coolers etc that we do not provide but I have a local vendor that delivers and picks up these items and charges a few dollars per day for each item, and give me a 20% referral.