You can be sure they will continue to negotiate for, strategize and advise themselves.If the laws are similar where you are, you should consider if you want someone doing those things for you, and whether you are comfortable going toe-to-toe alone with a licensed professional on a $1.25 million purchase.

I just couldn’t get comfortable with the numbers on this one. 

(This well could be a generational thing and whatever the comfort level of the guest is.)

Communicate with your tenant on tasks you are uncertain about and confirm if there are comfortable living with fixes you completed or if they would like a professional.

Are you comfortable with roommates?

Personally I wouldn't feel comfortable trying to wholesale a relatives $1M home knowing that I am breaking the law if I cross over into doing anything that can be considered representing them in the transaction, and knowing it will only be marketed to people who buy properties wholesale (typically investors who don't want to pay retail prices), instead of the majority of retail buyers active in the market who are typcially willing to pay more. 

If you go RBTR, here are a few key criteria I've seen to assure comfort of living and lower vacancy / turnover:- at least 400sqft per tenant and no more than 2 tenants to 1 full bath -excess parking where folks aren't blocking each other in and you're not getting complaints from your neighbors about overtaking the street parking.

And the locals in Highlands have been fiercely debating STR's and regulations for the last few years, so I wouldn't be comfortable buying there.

I saw a lot of advice to do what feels comfortable but I feel like I want to find out which one will end with more net worth.

I would suggest getting another full-time job for the time being and investing/doing STR on the side until you can fully and comfortably replace the income that you would be receiving from your job.Is your LTR in need of repair?