And with a good chance that I could be in a higher tax bracket in the year that I sell, it seems like I could actually lose money by taking the accelerated depreciation.Alternatively, could I write it off as sold for $0 (or essentially given away), since it wasn't listed in the contract, and the buyer will not likely be categorizing it as a separate item on their end?

Keep in mind the best assurance is the fact you are doing a good deal. all the agreements in the world won't protect them from losing money on a bad deal. 

I am also seeing condos losing value and that could be a way out however it has its own rules, fees that I will be stuck with. 

The lose of a loved one.

Note, even if insurance pays for all the damage your property suffers, you still lose.

If you are going to dabble at this things will be great until they are not and then you risk losing the handyman work as well. 

This usually entails losing cashflow but you get the property and the experience.

Rest due at closing) You can look at it anyway you want, but while you're looking, don't miss these financial facts:1- Cost to you = $63,6802 - Profit = $20,0003 - Remaining Cost not recovered = $43,680 (you don't make a profit until you recover all your costs, so the $20k "profit" in Item #1 isn't a profit...unless you think going to Vegas with $10k in cash, increasing your cash to $15k, then losing $30k is somehow winning $5k)4 - If, as mentioned above, you can get $350/month ($4200/yr) in rent...which if you were breaking even before, you would now be cash flowing $4300/year.5 - Unfortunately, that means it will still take you 10+ years (all being perfect) to recover the rest of your cost.6 - Still not a good deal...at all.

This makes your offer as strong as possible without putting yourself in a position to lose your earnest money. 

You lose if they make a fuss.