Feeling very defeated from this being our first investment.

So, what counts as itemized deductions?

Househacks make fine sense, even STRs if they're turn key, I understand the BRRRR methodology, but fixing sad houses and flipping em is what I look forward to most (aside from just being a numbers and data nerd) and yet I feel defeated before I've even started. 

Investment Info:

Small multi-family (2-4 units) buy & hold investment.

Purchase price: $230,000

Cash invested: $50,000

Duplex

Also, these situations sometimes present good opportunities, if you can get those areas to count as legal sf after purchasing at a discount.Also, I used to be a local deputy assessor, so I have some insight into assessing as well.

It's better to replace together, with the other neighbor, or it may defeat the purpose and have a seam down the middle.

Courts or lenders in your state might not honor the same protections or structure, which defeats the point.What most investors in NH and similar states do instead is one of these:Form a Holding Company LLC (like “Courtney Properties, LLC”), and then...Either put all properties under that one LLC (less protection, more simple), or...Form separate LLCs for each property (stronger protection, more paperwork and cost), and have them all owned by the holding company.As for naming — keep it simple, professional, and scalable.

I won’t go into a long backstory, but there’s a real estate agent in Florida who still holds an active license despite being found guilty of 40 counts of money laundering and 49 counts of health care fraud.

In a more specific scenario, if I house hack a duplex and have to pay a portion of any expenses out of pocket, does that count as what you described as negative rent?

No Kids.Income: $160kRetirement Savings: ~$900kHome Equity: $250kCash: ~$130k not counting windfall.Debt: $203k on mortgage at 5.125%.Recently inherited $175k.