It does feel like there is likely a major market correction coming, but due to limited inventory of vacation-rentable units in Maui I feel like I should be somewhat more protected from the effects of said recession.

Maintain detailed records of all renovation expenses to substantiate deductions and ensure compliance.This post does not create a CPA-Client relationship.

This was perfect to save a lot of money while maintaining a high standard of living.

Tools like Baselane simplifies bookkeeping and tax preparation by categorizing transactions and storing records.Keep personal and business accounts separate to maintain LLC liability protection.Please don't use the same LLC for flips and rentals.

the market is unforgiving right now, and if you buy a random property by looking on Zillow and turn it over to people you don't know to manage, you'll lose money.with respect to your specific question, if the property is safe, clean, and priced correctly, it will rent. but that doesn't mean you'll make money on it. 

They market it , rent it and maintain it for you but they keep 50% of your profits and limit you from using it for more than a few months a year  under their contracts , contracts are usually for 3 years , if you put it there you can not pull it out.

- How can I best estimate a breakeven point, and what techniques help maintain positive cash flow through all stages?

Like "renting to section 8 tenants is actually really easy", "your agent is not on your team just connect with people like me doing hundreds of deals every day and use my team instead", that hood properties will have "15-25% net caps" for beginner out of state investors when in reality they will definitely lose money every month due to the rent not being enough $ to maintain a rental property, never mind all the tenant issues involved with this property class or the difficulty of managing them remotely... but he's done thousands of them just this week while sitting on the beach in Florida... 

However, I know that I do not want all my income to be reliant on my day job and live to watch my retirement account grow.I am probably doing better than a lot of people my age but am eager to take the correct steps to build a real estate portfolio.

@Dennis Boettjer - everyone's comments above are correct.