You want to find a lender for this that specializes in STR financing!

I have Section 8 rentals in my portfolio but I do recommend connecting with a property manager who specializes in Section 8 rentals - they'll know all the specific requirements, inspections, and paperwork needed. 

Also when you are under contract and get condo docs, make sure to read the meeting minutes (for the past year if available) they will indicate if there are any talks of an upcoming special assessment (which you don't want).

That is a tough question to answer.In our case we get the most compliments on the lake and our kitchen.

I have one that is awesome and smart and specializes in Real Estate tax planning mostly because he is an investor as well so he is really good at what he does.  

The weekly rentals were $8,000 (June) & $8,500 (July-August) As the summer season rental is approaching us, we are faced with a tough decision.

Quote from @Kevin Robert Highgate: The ability to invest in property and replace your W2 income quickly is tough.

If you dont have the tools and skills to DIY and get yourself out of a tough spot then you can be SOL if the deal goes south.

STR markets are tough and change fast, best of luck!

Keep in mind that this is also a very tough time to be entering the market as an agent because the inventory is so low.