The way to win in real estate is to buy good assets over time and to never be a forced seller or a forced buyer.

I'm a Boston University college student, and I don't want to live in the dorms anymore, so I'm planning on using the rent-to-own strategy to find a place to stay as well as to use for househacking.

Take the time to understand the markets, explore different strategies, and build a solid foundation of knowledge. 

What strategies or tools do you seasoned landlords use to manage this kind of stress?

Learn how to calculate what a property will cash flow.If you are interested using the BRRRR strategy and haven't gone through the book already, I'd highly recommend listening to on Audible or reading the hardcopy of the book.

HELOCs tied to prime have the risk of getting higher when it comes to the payment, yes - you have the flexibility to take and repay as you wish over time but in the long run the refi would win IMO in this strategy.

In regards to the pricing strategy of the top performing listings in Music Row, I have attached below a chart representing how their daily rates vary thoughout the year for a 7-day booking: I did the same with the cleaning fee (per day of booking) below: With all these figures, I build a financial case study for a 1 bed / 1 bath property listed in Zillow at $385,000. 

Nothing wrong with that just is a fairly simple strategy.

He also is helping me build my portfolio through tax strategy.

A lender is going to look at your experience, knowledge, and strategy when making the decision to lend money to purchase real estate.Good Luck and stay engaged!