I created the following decision tree diagram to illustrate the decision process (click to enlarge).The above decision process is based on the property’s performance record, with the goal of achieving financial freedom in mind.Financial freedom is not just replacing your current income.

That means making calculated numbers based decisions, not emotional ones.

What information I should be analyzing to help me make a decision on where I should start.  

When money clouds decisions, ethics are often the first casualty.

It’s things like that which make this decision more than just a legal one-it’s about how organized you can be.Something else to consider: lenders often want you to personally guarantee loans, even if the property is in an LLC.

When representing Buyers my goal is to explain why properties are listed the way they are, and where I think the property will trade for, or sale at.

Fourth: even if the entire deduction is available, it results in much smaller automobile deductions in future years and extra taxable income when you sell the vehicle or trade it in.

@Chris Kay beleive you can do DSR loans without a job as they qualify the property, not the borrower.You'd still need 20-25% down though.That's where you have a decision:- Pay down the mortgage, setting yourself up for a future refinance to free up your VA Entitlement.OR- Save up for your next acquisition.Only YOU can make that decision as you have to be comfortable with the increasing debt-load risk and the additional time to manage everything.

A shorter minimum stay and dynamic pricing are great for attracting bookings during slower periods, though the trade-off with single-night weekend stays is definitely a balancing act.

I think the decision to seek cash flow over appreciation can be misguided because the best looking cash flow won't stay that way.