I agree that is will be a gamble as to how well it will do.Also, ask the owner if they will entertain partial owner financing to keep from dragging family and friends into this risky business venture.Maybe even rent from owner for a year with right to sublease to see how it goes before committing to a purchase.

The GC is a business person who doesn't care about your ARV, LTV, or your budget.

Make sure you talk to a Banker or Loan officer that is well versed in both SE (Self Employed) income and also Non/QM programs.One tip I will give you as a Banker is open up a "Business Checking account" and for the next 12 months pay "Everything" out of that account. 

Unfortunately, the tenant didn’t think me showing up to have a brief conversation was important enough to fit me in her busy schedule.

That said, I can handle it when necessary and have successfully built multiple self-started businesses and ventures in real estate investing (REI).

Looking to connect with other working parents who started this business adventure in their early 40's and made it work!

What type of business do you own?

If they work independently, set their schedule, and use their resources, they might qualify as a 1099 contractor, but misclassification risks IRS penalties.Wages for W-2 employees and payments to 1099 contractors are both deductible business expenses, but compliance is key.This post does not create a CPA-Client relationship.

The vacation side is more of a business and requires a lot more work but the affordable housing side is less labor intensive. 

Quote from @Rafael Ramos: I’m Rafael, a business owner based in Florida, and I’m looking for some advice to craft the best real estate investment strategy.