I wanted to start by house hacking but (1) I am not allowed due to strict HOA rules and (2) my city isn't as desired as the next city over.

I do not have an answer to that question, though as a landlord those VA's annoy the you know what out of me constantly...That said, I am an end buyer once you get those houses under contract! 

These are a list of my lessons and challenges along the way:*Pay someone to rip up the tile in a house!

I am not sure which market to look into as right now I am currently in new york and was told my best bet for cash flow would be to look oos for deals that I could use as a rental or house hack.

If they are planning on adding hundreds of new student housing units that could decrease rents for a few years. 

Ask for advice before going into these "investment" tools; not after.I will always recommend that YOU should own your real estate, and not get involved with these crummy and questionable deals.If one cannot afford to buy their own real estate, purchase the Vanguard REIT and save until you have the down payment for a house hack or investment property. 

I am looking to buy a duplex in the Houston area and house hack the property.

Also have some experience in ground up, but large lake houses versus MFH. 

Wonder if anyone has run into the issue I'm havingMy wife and her parents went in on a duplex together and the three of them are all on the title and loan.My wife and I are in escrow on a house in Citrus Heights.

This is like worrying about an asteroid hitting your house.