@Flavia Vangelotti With your expressed concern for cash flow, I suggest considering a Debt-Service Coverage Ratio (DSCR) loan.

Or use their suggested point of entry and reconfigure the footprint.What does their "Better" entry mean to your project footprint?

I'd like to check into using a property management company for my first property, then I'll add it to my second.

Looking to take the next steps in finding, funding, rehabbing, and flip or holding additional properties. 

If it's done right and the layout makes sense you recover your money on the added value of the house, not in the monthly additional rent.

I'd suggest running your numbers based on a few scenarios to see what works best for your overall goals for the property. 

Additionally, getting in with a local broker helps as they can shop around for you.Umbrella insurance is pretty cheap to add on in my experience, so I think it’s worth it.

AKA it is a way to access some of the money you've put into your home while also making sure you can still afford your mortgage payments and other debts.You will need a renter in place as rental income is apart of the calculations when underwriting these loans in addition to the other factors you mentioned like monthly housing expenses (PITIA: principle, interest, taxes, insurance, assocaited fees ARV, debt outstanding.

Certainly open to other ideas and strategies, it would just require additional diligence from my end given my level of comfort and expertise would be lacking in other areas.

Can you convert it back to an Airbnb for additional income and use the proposed rents to offset the mortgage so you can buy your new home?