Tax Plan for SFH Flip

[Andrew S.]

For context: I have successfully "flipped" three houses in the past 7-8 years, all of which were my primary residence. I'm about to receive the contract on a SFH in NY state (buying outright with cash) with the plan to rehab and sell it next year, but this is the first one that will be truly an investment/business property and not my home. I wanted to see if you could poke any holes in my plan, and also have a few questions at the bottom.

1) I plan to hold the property in a single member NY LLC that I own, have its own bank account, run all costs through it, etc, to separate the liability from my personal assets. It sounds like some argue that this type of situation is grey in terms of the actual legal separation created, but I've been advised if it is handled properly and above board, this is the way to go.

2) My CPA has advised that from a tax perspective, there is little/no difference than owning the house personally. Capital improvements increase the basis of the house, reducing the capital gains of the sale. Any gains flow through the LLC to my personal return. Given the cash purchase and low property taxes, holding costs are low enough that I potentially plan to hold the house for a year to make the gains long term, but not set on this. I'm not planning on it, but a 1031 for another property afterwards is not out of the question.

Questions: 

-Is there any difference between signing/fulfilling the contract as an LLC vs signing personally and transferring property to LLC? I plan to discuss this with my attorney today, but curious of any experience here.

-How does homeowners work with an LLC? Will most insurers work the same way as primary residence in this situation? Any other insurance I should consider getting?

-Is maintenance deductible as a business expense in this situation? I believe my CPA said it can only be used to offset rental income, but I wasn't sure.

-There is a world where the rehab is done by next summer, in which case I would consider doing a summer rental (very viable in the area) before selling after the year is up. Would rental income change any of the above plan? 

Any other thoughts on tax minimization would be most appreciated. I don't qualify for RE professional status, and I will be active, so any IRA-related purchase is out of the question, but looking for anything else I should be thinking about. Thanks!