I don’t mean to be pessimistic but if you do decide to sell now you will take a pretty big hit on the home. Without running comps I would say you could see anywhere from a small loss to perhaps up to 20%.
Answering the questions that you posed is not to hard. It is easy to map out a simple spread sheet that can predict appreciation or depreciation over several years. I have that. The tricky part is trying to estimate the numbers. It is very likely that if you sell in 3 years you will suffer a larger loss then if you sell now. However I only say that because my “opinion” which is not worth much, is that the market will continue to go down. In 3 years it may have hit bottom or even before that point, however it will not have recovered to where it is today, (at least for homes in north park). In 5 years that is a bit harder to say. I do believe we will be back on the upswing in 5 years but will your home be worth more in 5 years then it is today? It all depends on how far we go until we hit bottom, and how flat we stay when we are at bottom, and how fast we rise when we begin to appreciate again. All of these factors of course are influenced by interest rates.
By now your eyes should be sufficiently glazed over.
If you want to run some “simulations” so to speak I can pose some easy numbers for you and post them. The thing is that the answers to all of your questions will be based on whatever numbers we use right? If you want to suppose 7% down for the next few years I can give you EXACT answers to your questions. However if 7% down is not what happens, then our answers will be off base.
Some people here are more bearish then I, a few are less bearish. Some will say that 600/sf will never happen in NP again. Personally I am not sure but it seems like it may be a stretch. Perhaps consider just adding on to your home and buckling in for the very long run of 7-10 years? Otherwise I would take the bad medicine now, then rent for a year or two, then buy. There are alot of factors to consider though like family harmony and such.