Shane,
We definitely played against eachother at some point. I played at Seminole High, Northwest little league and for every travel team in pinellas county at some point. Happy to see you are still playing overseas! Congrats man, I hope all is going well.
It appears we have taken somewhat similar paths in life (minus overseas baseball). I am working in Finance also - but I also just completed my first house hack. I purchased a triplex in Madeira Beach and just completed my year of occupancy. You are ABSOLUTELY on the right path in pursuing a house hack to get started.
My input on your questions above... I would say you may be better off waiting for a house hack that you can qualify for yourself. Keep saving money for down payment and renovations and get your own deal from the get-go.
In terms of metrics I use to determine the quality of house hack investments...
I analyze in two pieces: 1. During occupancy period 2. as a rental property after moving out.
During the occupancy period I look at the savings of living there versus paying full rent elsewhere or paying a full mortgage for a SFH. Also I look at how much I can increase the rents in the other units in my first year. Also a major one for me is how much value can I add through renovations & improvements in year 1.
Part 2, analyzing as a rental property. Cash on cash return is #1 for me - and with a house hack, this number can be massive relative to a 20-25% down deal. Since we are young, location and appreciation potential is absolutely everything. The appreciation that can be generated by holding onto good properties here in Pinellas will be huge over our lifetimes. So while cash flow is important to get going, the appreciation potential is what really gets me excited about a deal.
Congrats again on where you have gotten, and on deciding to house hack! Keep it up man I wish you the best of luck.