I’m confident this is a great deal but would like to get some pointers/tips from seasoned investors.

Maybe that'll give me more confidence to manage this second property remotely + increase bookings of my current place. 

I just got engaged to my fiancé, who graduated college in May and has a considerable amount of debt.

I’m confident long term holds will present themselves along the way, I just need to focus on what can work in the next 12-24 months. 

That is a good point, and when I think of what makes me feel more confident in my first flip, it always has to do with mistakes around the rehab (cost miscalculated and time lines)  

Many speculative investors with over confident numbers purchased short terms rentals in Hot Spots near national parks based on the returns of a short term rental.

I’m still in the shallow end of the beach, focusing on helping fund EMDs on deals while I learn to dive deeper, achieve greater confidence to eventually swim with the dolphins and whales.

I agree with just about everyone above that the price should be either discussed upfront or in the engagement letter before services began.It's different to know how much they saved you because tax preparation typically isn't a service to save you taxes, you'll want to meet with them during the year for this.

Public has confidence in economy) and (4) OVER SUPPLY (Due to expansion, supply is now starting to exceed demand. 

If I was confident in being able to make 10%+ return in real estate(Cash Flow + Appreciation), then yes.I don't know if I would do it now since i am not sure I can make a 10%+ return in real estate given where interest rates are.The reason I suggest 10% is because the stock market on average makes 8% annually.The 2% annual difference will pay for the penalty over several years.