LLC electing S-Corp status is usually beneficial when flipping houses, but be careful that your CPA helps you with the "reasonable compensation" aspect- as that would be the main audit risk.

@Daulton H.Get QBs -easier for accountants to do your taxes, better if you get audited, better if bank wants financials, etc.

Like many on here I have been asked to qualify stuff for the IRS and been audited too; when that happens he becomes my Rottweiler-everyone should have one of those!

Buying/redeeming gift cards for ones self and claiming it is abusing it and you are taking a risk by doing so if you get audited and fail to produce proof.

Splitting your property into allocation methodology will not hold up for any audit. 

-What is the best system to be best prepared come tax season as far as having everything organized for my CPA and having the documentation I need in case of an audit?

I've fixed pretty much everything unless it was over my skill set (replacing capacitor on A/C system, for instance; landlord told me when I moved in it was okay to repaint or whatever as long as it improved the house), my neighbors love me - they've told him so; I've resodded the yard twice (FL grass sucks with a dog), had the landscape crew redo the trees in front so they look good, replanted flower beds (perennials), power washed the house every year after wet season ended, ensured the pest control worked...The BUT part ...As a sole practioning consultant (pre-IPO weakness remediation, large financial systems implementations, global audit recommendations for SEC registrants, etc.) at times during the last 3 years things have been sink or sink lower credit wise and the ID theft didn't help (apparently, I bought a car in GA and own some property in TX).

Initial cap rate looks good but I'd suggest making any offer subject to verification of rent (audit) and interior walk through - pretty standard. 

Most HOAs are required to get a professional financial audit and file a tax return each year and then there may be legal fees to collect back dues from people who aren't paying.There is a LOT that goes on behind the scenes in an HOA. 

Any change always has the potential to raise questions in an audit.