I decided to gamble on appreciation and overbid on a duplex that will have good cash flow in Oak Park after losing another all cash deal (I bid all cash, over asking and was outbid by a buyer with similar terms with an offer “well above” mine on a different property in the same neighborhood. 

Personally, if given the opportunity to start anew, I would pursue this approach, as it offers numerous benefits.

If you're counting on appreciation, then you're gambling - doesn't matter where we're at in a Real Estate cycle.

Therefore, she's not going anywhere in May unless she wants to.I'd inform the tenant that you have incurred numerous costs with advertising and time spent marketing/showing the unit and had to decline a new tenant at a higher rent.

I had numerous electricians tell me the old knob and tube was ok, but I will be replacing all of it in the future for piece of mind.

If AirBNB were a franchise instead of a platform, they would be in violation of numerous franchising laws and regulations.

This should tell you numerically what makes more sense investment wise........With that said, in most cases, all that really matters is that you live in the house that makes you happy and that you can sleep well at night.

They were gambling that the yield curve wouldn’t invert like it did, but then it did, and hard. 

That being said, this can be very successful in the sense of having numerous tenants interested in housing in a college town such as Gainesville, but I'd be cautious with who the tenants are.

Truth is it takes a LOT of “grunt” work, or the capital to pay someone to do the repetitive work of cold calling, answering inquiries, drawing up numerous offers that will never be accepted, sending out property sale notices to buyers that will never complete the purchase and will attempt to go around you directly to the seller, addressing post cards, placing “bandit” signs, etc.