Quote from @Bill B.:
More important than what you owe on your current home is why are you moving and what did you pay for it.
If you’re moving for a lifestyle upgrade or other non-financial reason go ahead and move. (Since it sounds like the new home is more expensive.)
Now the important question is what did you pay for it? If you have a gain over a couple hundred thousand I’d’ pry sell. Every $100k in gain up to the limits, $250k (if single) or $500k (if married) will save you $15k in federal taxes and I’m guessing $5-10k in state taxes? So if you have $200k in gains you’d have to make $50k on your rental NET, after expenses. So you can pay $10k in taxes and be back to where you would be today by selling. Except you’d also have to make up the interest expenses on that extra $500k you borrow, so you have to make that plus $2,500/mo profit (another $30k) to pay the interest.
So if you think you can net say $45k/yr in profit it will take you 3 years to break even if you ignore income taxes. Most rentals won’t bring in $4k/mo in profits. (Not rent, profits after expenses.)
Ok so I'll be netting more then $250k in capital gains. I have two questions, any home improvements I made like finishing my basement I know I can add to the cost basis of the home, do I need to have receipts for all my drywall, lumber , etc or can I just use a good faith estimate? Also, if I plan to apply that equity to the new home in a form of down payment, am I still taxed? Obviosuly trying to find a way to negate taxes on the cap gains over the $250k limit.