At 59 you can look at investing for supplemental cash flow. 

At 33 years old my wife and I have decided to look into building up a real estate portfolio to help supplement and possibly bring about sooner my retirement.Just to be clear I am very happy in my career and am not looking to quit my job.

I am considering supplementing the 650 with an additional 350 of SFR, absentee, with high equity, to bring my total back up to around 1000 names.So here are my questions:1.

Since you are now supplementing your tenants rent it will be to your advantage to find a new tenant if you can transition smoothly.

Our goal is to generate supplemental income overtime but its also important to us that the property value appreciates over time too. 

As much as I'd like to begin supplementing my income, one or even two C class buildings wouldn't be able to do that for me. 

What did you have supplemental income when you started?

Short term: I'm trying to help my dad get enough supplemental income that he can quit his salaried job and focus full time on his farm land/hunting property business. 

Big is different for everyone of course, but for me I'm talking 1.5M-2M ARV, and I would use as much investor capital as possible for the purchase and rehab in exchange for a slice of equity to supplement their cash flow on the back end.

VRBO, however, does allow supplemental rental agreements.