We fell in love with the location and turned our downtown houses into a rental instead - and we now occupy the lakehouse.

I looked at few houses in Bell Air community but I found it difficult to even break even with mortgage.

@Travis Andres @Brian Malavsky If you're looking for AI messaging, my team has developed an in-house PMS that is now public called Hostvana (hostvana.io) who's core competency is messaging (along with free lock integration and other features) and is more advanced than Hospitable's for a very affordable price.Here are some recent replies in my personal account inbox:https://ibb.co/nk8KWbR (cleaning fee policy question)https://ibb.co/sgP0qmr (parking question and check on status)https://ibb.co/HCKVPd8 (random question answered with previous context)https://ibb.co/gv0tY16 (early check-in reply after checking calendar.

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! 

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.

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

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

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

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.