I am in Illinois, so that may be the easiest place for me to learn the game.

The bad news is that it will be harder for you to execute your plan to raise rents and refinance, taking out the seller and recovering part or all of your down payment because the lower LTV that lenders will constrain you to will pigeonhole you.Another challenge to be aware of is that there are likely HOA dues—typically if only one unit is owned by a third party the HOA is formed and collects dues even from the developer-owned units.

The first in Santa Rosa have created an increasingly large housing shortage, providing opportunity to developers. 

Once you are out of the bad deal, you can take the cash you do get out of it, and invest in a property that will make money...meaning, you will recover the temporary losses you have now, and start making a profit again.Staying with a bad hand, and continuously "betting on it", will get you out of the game fast. 

A developer is now building a big apartment building behind us.

IDEALLY I would love to find an investor who basically has been doing this and wants skin in the game but does not want to deal with the head aches of the construction or management side.

All the more argument for developing your own PM company.

Not sure if the long game will be better if I hold onto this first home, I’ve currently been living in it 2 years.

Hi, what is your in-put with Lincoln Yard development and the city project around the Chicago River also, which area in the city you think is the best to flip? 

Ah, loving this thread with all the speculation regarding the AU NZ and Canadian property market :)Having been a property investor and developer here in Australia for over 15 years, I can attest that the market is extremely expensive, mainly in the east coast capitals (Melbourne, Sydney particularly) and the rental returns on residential are quite low, I can also assure you there is no "imminent" collapse  just around the corner.