Whether to go with a BRRRR deal or multiple down payments depends on your risk tolerance and long-term strategy.

I think you have to find what your strengths are and what your risk tolerance is in different areas of RE and look at your entire financial picture.  

Quote from @Ryan Harrell: Hi Benjamin, The answers to your questions ultimately depend on your risk tolerance and investing goals.

What is your Risk tolerance level?

This can put a significant strain on your finances and cash flowThey also often require a large down payment themselves and may have a strict repayment schedule that can be difficult to meet, especially if there are unforeseen circumstances or delays in renting the property or generating income from itIn addition, relying on this type of loan may expose you to higher financial stress and the possibility of default if you are unable to meet your loan obligationsThe final decision depends on your overall financial situation, risk tolerance, and your ability to manage the associated costs and obligations

I think this depends on your risk tolerance and your interest rate.  

However, if you want to maximize equity and control every step of the process, doing it yourself might be better.At the end of the day, it’s about what fits your goals and risk tolerance.

Quote from @Paul De Luca:Personally, I'm not a fan of enabling bad tenant behavior and in life you get what you tolerate.

But that's just me, maybe your market can tolerate higher nightly rates.....I agree with Bruce.

It seems like you have some very solid goals of multiple income streams, and a well calibrated risk tolerance.