Jimmy Klein  Evan,A flagged property is a "branded" hotel like one in the Marriott, Hilton, Hyatt, or even "lesser" brands.

A two-family where you live in one side and rent your other rooms to friends and then rent the other side (maybe even do mid-term rental or short-term) with a much lower downpayment is potentially a better producer.

At $300/door you would need 17 or so doors to  do that… and even then you won’t clear all that with reserves you will want to set aside.  

As an individual not comfortable with other people paying my bills I struggle to be an individual who might allow another person to take over payments and have the unknown idea of an unforseen even happening and my personal credit becoming ruined.Sellers in foreclosure typically have NO issue with me taking over their loan payments.

Or do you simply have to be obsessed to even have a chance to make it in this business?

.- I have about 150K available for a down payment, any suggestions on the type of property to target (cabin, condo) if the goal is to be around cash flow even?

Many HELOC or second mortgages are fixed interest rates and depending on the loan amount, even offer 100% online and no appraisal requirement for issuance.

Even nextdoor can helphttps://nextdoor.com/pages/steve-oneill-wimberley-tx/

I'd recommend mixing in more commercial to balance out multiple assets, buy a liquor license for a few hundred thousand, etc to make the deal work a little better. columbus hospitality isn't as strong unless you are in the urban core but even then I'd go for a lower risk asset class like multifamily and retail mixed use. hotel is very strong operator but management intensive.

I will need to finance most of the purchase, but if my numbers are correct, it would still generate cash flow even with 100% financing.