I would go with the FHA first because you plan to house hack it anyway because you are taking what is currently presumably your housing expense and reducing or eliminating it. 

I took way too many risks, did way too little DD on most deals. 

You are looking at a extreamly high risk gamble regardless of your past experience.

And has the same long term goals as me (both young 20s and want to replace our current work income with passive to travel).I'm looking for advice on the risks of investing it in real estate (currently in stocks and bonds).

Rent to price ratio should be viewed as an assesment of the risk of the property and market.

You need to have a good agreement vetted by an experienced professional.If one partner puts in more money than the other, you could change ownership interests, you could treat it as a loan, you could reduce income/profits from the non-contributing partner until the contributing partner is paid, etc.You will want to discuss with each other who will be doing what management functions and whether that is worth anything to you both. 

ok so NO I DO NOT think you should consider buying this home.... first of all i think your numbers are off, insurance on $500K home is way more than $50 a month...also you will need 20% ($90,000) for down payment if purchase price is 450,000......then you also need to consider other expenses like vacancy, repairs, property management (even if you self manage)..... as your first deal this is way too much risk for negative cash flow and the hopes of appreciation........if its still sitting on the market, then its over priced....... an appreciation play is not a smart first investment IMO

Are there risks involved in submitting a claim, or should I definitely submit a claim an I am overthinking this? 

C class is very high risk and management intensive. $3200 rent on a 300K C class property is way too low.

C can come with higher cash flow for certain periods but it can also come with increased risk & potential downside loss.