I would immediately begin investing with your family, as you have the credibility and net worth elements that stop most newbies taken care off. 

I didn’t have a ton of inventory when the market turned out here either, which helped some compared to other investors flipping homes, but if looking to flip and worried about market drops, this is a strategy that works out here.

Pay is comparable and living in KC will allow me to build a solid portfolio over the next 4-8 years, allowing me to effectively buy enough cash flow.It's been my only major step toward cutting my expenses, but what market you live in is HUGE, especially when you're talking living in a extremely pricey one.Meal preping my lunches and dinners for the week has helped save a lot of money.Like @Jay Hinrichs i too am a mileage junkie.

The pro forma statements are based on the income and expenses of comparable homes currently being short term rented.4) HOA fees do vary from $500+ per month to zero. 

Look at what your competition is doing and price comparably.

I've looked in Southern Maine and regionally and yes our prices are depressed comparatively but it still might not be a "deal."

The house is not in my ideal neighborhood but with the initial numbers it would be worth buying.So more important question is if I want to deal with "average deal" house in this neghborhood compared to "great deal" house as it initially was.I guess I have some thinking to do too. :-)

Interest rates would be comparable to a primary residence mortgage.You can find some smaller or regional banks that would lend to an LLC but I’ve found the interest rates to be at least 1.0% higher than conventional.

I think you'll find that lenders can be dramatically different from one another, especially when comparing national banks to local banks and credit unions.I would say visit a couple more banks, be forthcoming with your situation, and see what they say.

The low income element, with SEC 8 or not, makes screening harder, maintaining harder, and collecting harder.