New to Real Estate, Looking for detailed advice

[Mike Allen]

*** I just read the rules and see that it says no requests for mentors. I am not sure if what I have asked for here counts as that, so please feel free to delete the post if it violates that rule. I AM asking for help from some individual in looking through the specifics of this deal, or someone who can point me toward a calculator of some sort that combines the househacking/STR combo that I am considering with this deal.***

 I have been browsing these forums and binge-watching YouTube and BP Podcasts for the last ~4-6 weeks and my wife and I are both on board to try our hand at real estate investing.

I believe I have found a deal that works for us, but would love the opportunity to talk through it with someone who knows what they are talking about before pulling the trigger, because it seems like it is a bit outside nearly all of the examples I have seen other people describe as their first deals.

The property has a house on two and a half acres that also comes with three rental cabins (they are currently being used as short term rental units). The area is on the NC side of the Great Smokey Mountain National Park. 

Our plan would be to sell our current home and move into the primary home and then manage the cabins as short term rentals. At least one of us should be able to continue working remotely (how do others get health insurance without working a normal job?) and I spoke with the bank earlier today and confirmed that we should qualify for a jumbo loan that would allow us to make this work out.

The place I am getting stuck is trying to figure out any kind of realistic estimates for whether the three cabins are actually able to generate enough positive cashflow to allow us to eventually step back from our jobs and/or running the numbers for everything in a way that I would feel confident enough to try commit to something like this.

Would it make better sense to try and start out with something more simple/conservative?

Thanks, in advance, for any thoughts or advice!