Difficulty Selling Properties to Free Market again, NOT correct. most investors want sec 8 tenants in.

(If it will be easier to sell sooner in season.)

I have been involved in the buying and selling of portfolios of land notes for over 8 years.  

In general, this forces the person inheriting the property to sell.  

They are asking for a sell price??

I would definitely hire a management company if I plan to rent the property.Back up plan is to stay there two years, sell the property and avoid paying taxes.Fellow BiggerPockets community, I would love some advice on evaluating whether I should flip the property to reinvest in a bigger home or multifamily unit or rent the property with a management company?

Your basis in the home is not going to change so when you sell you're still going to recapture depreciation and pay capital gains unless you 1031 or you don't have any gains.2.

say you budget for a 3 month rehab and it takes 7 and you break even after you sell. 

In a few months, I will be selling my home.

Yes, but it cannot be in an LLC as then the taxpayer would be different on the purchase side vs the sell side of the 1031 exchange.