First Move-I'm Contemplating- Short Term Rental

[Alex Gauthier]

Hey folks, my very first post but I'm suddenly very motivated by changing job circumstances (not getting laid off at least not right now) and hoping this community is as welcoming and helpful as the podcast and books I'm reading claim! :-). We do have about $12,000 in credit card debt to deal with in this process but no car payments or other liabilities other than a cheap house payment and normal monthly bills.

I have an R2 zoned property where I live with my family. It has a 700sqft workshop in the back separate from the house. I'm thinking as my first move in this new venture to do something like this in the next 12-18 months, in this order. Open to suggestions, applause, criticism and mentorship. Please jump in!

1. Finish current bathroom remodel of main house by end of July
2. Cash out refi to partially fund 700sqft Air BnB construction in what is now that back workshop. (end of august)
3. Start renting it. (estimate something like $2000/mo cashflow after fees and expenses. (construction time dependent... spring 2022?)
4. Re-fi again with new property improvements taken into account (spring 2022)
5. Move family into a bigger house using cashflow from rental to finance downpayment- may look for something that we can get cheap and renovate before we move (summer 2022)
6. Re-model existing house and get it going as a short or long term rental as well. (So I'd have the Air BnB plus another long term or short term rental on the same property). Cash flow from original property probably closer to $4000/mo after expenses assuming I can do two short terms on the same property. (fall 2022)

This would then put me in a situation where both the payments on the original property plus the new one we would move to are covered before leaving some good cashflow still before considering mine and m wife's income (figure around $125k/year.. From here, I would expand into BRRRs or other opportunities that I'm only now starting to learn more about.

I pose this question here because it all seems so simple, and I know there are taxes, unexpected expenses, making some mistakes, legal ignorance on my part etc that could all derail this plan. So I'm kind of hoping for encouragement/reality check from anyone that has some experience in a situation like this. (hope this question isn't too long)

I hope this doesn't come across as asking for a mentor which I understand is not appropriate... just looking for feedback from the community on whether this seems like a sound way to get started.