On your business units, you have a capital gain of $100k (2 x $150k - $200k) which is taxable.I intentionally did not address depreciation or closing costs, to not make it more complicated.

@Jay Hinrichs:Thanks for the note re private investors - This seems a little more complicated that the basic stuff I've gotten through the BP site, so I don't know what I don't know - appreciate the help.

Account ClosedThe answer to your question can be very simple or very complicated, depending on what your business is, how well it is going, your overall financials and your family's handling of money.I'll give you the simple answer, which is based on these assumptions:you file a joint tax returnyour business is moderately profitableyou both are working in this business, more or less equallythere're no special circumstances making things more complicatedIn this case, just like with you being a sole proprietor in the past, your taxes are incurred when the money comes into your company, not when you take it out.

@Gary Kinder To be clear, that would be in a non judicial foreclosure....for a judicial foreclosure you have to have time to schedule a hearing and have the judge agree. 

I could teach someone else do it and pay them $20/hr and get it done in 2 hours each.Replacing a window is neither complicated nor difficult.

I’m not sure what the laws are where you live but we generally don’t accept partial payments because it complicates a potential eviction.

I’ve tried many and have taken my properties back every time; and I’m local.Air bnb will be extremely complicated without a 24x7 manager and cleaning/maintenance team...we just don’t have these companies in place and certainly not in abundance. 2-Self managing in Buffalo is allowed, but you have to have a local property contact registered with the city of Buffalo rental registry.  

@Josh Rogers It was semi-complicated but in the end, we had assets to help value the business worth.

Unfortunately the person who managed the project (Andrea) is having some health complications but his father who owns the company is still available.

Not likely, both the lender and the court, if it is a judicial foreclosure, would have to agree.If you had a little more time, were actually buying with cash you could document....maybe.