I don't NEED to sell (no financial or other dire circumstance), but aspire to UPGRADE to nicer / waterfront / dream / forever home. 

I live overseas, but I own a rental property which I owe 240k and is worth 345k. My goal is to apply for a HELOC for a downpayment on another investment property. Is it realistic to get at least 10k from this strategy...

Give us deal details, location, partner dynamics, a good grasp on the numbers, life circumstances (about to have a baby? 

The last thing in the world you want to do is commit mortgage fraud under any circumstances obviously.

The entire point of a contract is that the parties agree to uphold the 4-corners of it, even if their personal circumstances change. 

Chaining is not allowed in any circumstance. 

I have read that there are some qualifying events / extenuating circumstances that may allow you to obtain FHA approval after 1yr from the date of title transfer post short sale?

These things will also cause complications if you need to sell as title will find out about liens on the title search or owed dues/fines/fees on the estoppel letter.As others have mentioned, the annual dues shouldn't fluctuate much, plus you should be a member of the HOA and have some say in the HOA budget.Now special assessments are different circumstances, and probably not something you could ever get a tenant to cover (and probably won't be able to predict much to change a lease ahead of time).

Generally, I'd say no, it isn't a good idea to do what you are thinking, but depending on your specific circumstances, it might work for your plans.

I will approach all the good looking women that ask smart questions or provide great value to others... :)