I don't like the rules, lack of available financing should you decide to sell, 'surprise' assessments that the association springs on you and could hold up repairs and the ability to sell should the association decide not to make repairs.

You need a calm consistent demeanor and the ability to handle and solve problems and you have to effectively deal with lots of different personalities.

Would love to get second look over my assumptions, challenge/reveal any flaws in my current plan, and listen to any suggestions to successfully house hack in Austin, TX.Main Goal: House hack to live for free, cash-flow ~$150-200, have the ability to cash flow some after I plan to move out in a few years.My situation: Newbie and aspiring real estate investor looking to purchase my first deal at the end of 2020 (Ideally November/December).

I have stated perhaps hundreds of times in these forums that this city is unusual, not what most people expect, broken up by geography and history to a greater degree than many others.

I’m really struggling on crafting the appropriate rental agreement and wanting to provide a level of separation and degree of confidentiality between his roommates, mainly to avoid any potential interpersonal conflicts.

How capitalized are you (what is your ability to absorb big expenses if/when you have them like a major capex event)?

The other side to buying in almost all of CA right now is that evictions are not possible by any means, never mind rent control on top of it, but if you are adopting tenants in a 4 unit its not likely going to cash flow, and unless you have the ability to do cash for keys, and you have tenants willing to move then its another hurdle to cross. 

Happy to discuss what I've seen and the areas where people have found some success with some degree of mitigated risks. 

@Ry Eikleberry, The most critical component of success in any venture (and real estate is no exception) is your ability to draw a team around you. 

Even having a couple backup plans would help tremendously & increase your ability to make the best offer for you.