Hi @Tom Manna . You can pretty much always do Sub2, but the real question is how likely the loan is going to be called for violation of the due-on-sale clause (DoSC). Who's the lender for the $500K? Is it a large bank, a commercial lender, a small bank, an individual? Large lenders might be less likely to notice, provided you take appropriate steps like placing the property in a trust first.
If you've never done Sub2 before, I probably wouldn't start with a $2MM deal. Could you find a serious buyer with deep pockets looking for a great financed deal that could pay you a wholesale fee?