To Sell or Not to Sell?

 I have been considering selling my house in Oregon.

It is not because of bad tenants. It is quite the contrary. Mother Bing did well choosing the current tenants. They have been caring for it for 9 years. I have not been required to pay for repairs. I was asked early if repairs could be made and they withhold the amount and send a statement of the charges. I have received none but they have done replacements. They have expressed the desire to buy it.

The family renting it has three children who have been born there and know no other house to call home. The oldest child will have grown to adulthood before Jared retires and we return to Oregon. They have animals there they are fond of. One would not know they do not already own it by how they are living in it.

I understand their motivation for desiring this. They have lived there longer than I have. I am sure that when I returned to the house, what made it mine would be gone and it would look like hers. My connection is lost. Hers is firmly rooted there. Even my red door, which no Chinese home is without, has been repainted.

Of course, I will never get another deal on property as I did with that one. I bought it from my best friend with her "best friend" discount considerably under market value at the time. It makes me ask, If I were to sell, do I sell at current market and profit handsomely or do I sell it with the same level of discount I bought it with? Perhaps I could ask them what their offer is and work from there.

I believe I will ask a tax attorney some questions of this too. What is the point of selling and making a profit if the government is going to take half of it unless I reinvest it quickly. I have been told horror stories of large amounts being lost to taxation. Jared and I would like to have something to buy a new home once he retires.

Who would believe a house could cause such a head ache?