I did discuss with my accountant and he is unsure as he is not familiar with IRA rollover process. 

In my market there are 2 reasons that keeping is smart.  1) the historical long term appreciation is on going, going back to when records started tracking the appreciation 2) the property tax is near fixed cost.  

@Rebecca GonaBigger Pockets is a great place to find a tax accountant that specializes in short-term rentals. 

You'll need to have 10%  thru the sale account by 5pm the day of the win, and will have to pay the remainder within 15 days of the win.

@Hansen TongI recommend finding an accountant that specializes in real estate taxation.

For that, you'll want to ensure your LLC is already set up and approved in the state where you’re operating.Most lenders are fine with the funds coming from your personal account, especially if the LLC is newly formed.

:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+ (roughly 5% probability of default), zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680 (around 10% probability of default), some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.

Easy to transition this to a property manager, or even have multiple people run the account, than if the account is a personal account.

Jan and Feb are historically slow but a few suggestions I have are1.

Next, I'd get my electrician in there STAT to give me there quote to get it done. maximum scope, account for all variables, not a "hopefully it's just..."