Need Advice; short term rental use property in waikiki,hawaii

[Carmela Zaragoza]

hi all! super newb here but the husband and i are looking at ways to eventually move to oahu with two properties both paid for in cash, one to live in and one to rent out.

Situation: We currently have money from a previous home sale here in los angeles that we can use as a downpayment for a buy and hold property in waikiki that we can use for short term rental(airbnb,vrbo). the hope is that it can cashflow itself (for the most part) till paid off then we can sell our current property in los angeles to buy another property in oahu in cash.

The numbers: Our budget is around $185K with 20% down w/ maintenance (hoa) fee of max $1,000 per month w/ all utilities included. plus management fees and all other overhead cost that im really not familiar with in terms of purchasing a rental property in waikiki (taxes etc.)

My main question is, for those in the know, do you think we'll clear $2,000 a month enough to cover the mortgage plus maintenance fees? we make an ok enough income, no debt and frugal enough to cover any other overhead cost ( vacancies, maintenance, etc) that might arise. As always, i dont know what i dont know so any other information you can give me to paint a clearer picture would be greatly appreciated! Thanks so much!