If you really feel you must get this place get multiple quotes on the largest issues, write an extension to the inspection contingency and do more due diligence.  

Ultimately, my vision is partnering with a private lender so I can spread my funds across multiple deals at once and scale quicker; I'm really happy so far with my agents, contractor, and refi lender, so I feel like getting a great lender would be the next step for me.

They're experienced investors and some of them buy sight unseen in multiple states - they have a high risk tolerance. 

Contemplating buying a place near Destin.

I'd get a house with multiple bedrooms (4-5) and you can live for free or even cashflow with the rent you'll receive.

I'd rather pay less now with a higher rate that I can refi out of than wait until they are lower and pay more (and probably have worse terms in the contract too due to multiple offers).  

We're picking up extra work, multiple side-hustles and cutting living expenses... what am I missing here?! 

A well-maintained property not only attracts quality tenants but also helps preserve its market value.Time Management: Managing a rental property can be time-consuming, especially if you have multiple properties or are working another full-time job.

Multiple reasons why - high turnover, language barrier, individuals not representative of your brand, etc. 

I have seen multiple things happen that are unexplainable.