I have experience as a Residential agent in Denver, CO and as a commercial Leasing Associate in Chicago, IL.I am planning to purchase my first rental home here in the next year or so and make it my primary residence.

I also know I can look at ways of borrowing against that equity (HELOC for example) but I also just feel like if I take debt on that property the cashflow goes down, and then if the association also takes the loan it goes down more, and at that point I don't know why it would be a better option than selling before August. 

I am on the board of the RPA (Rental Property Association of Wisconsin, a non-profit) and typically hear if things like this are an issue from our members or attorneys.

You don't need to use your own capital or credit.Lower risk: Since you're not buying the property yourself, you're not taking on the risks associated with ownership, like vacancies or repairs.4.

A lot of the cost is associated with the drive to get out and back to our lake house.If your friend isn't listed on VRBO, she is missing out on revenue and bookings. 

The National Association of Realtors says that the average profit on a flip is is $15,000 and takes 6 months from start to sale.  

Any social groups which are associated with it, etc?

If you're lucky enough to get a free and clear property where the seller is willing to finance, this reduces much of the risk associated with seller-finance.I would make sure the title is then moved over to your name, especially since there is not a risk of a due-on-sale clause being triggered.

-- National Association of Realtors settled an anit-trust lawsuit last year.

Call a different number you found online associated with the same company, etc.