A near identical property with slightly better features (larger yard, driveway and a little prettier) sold a week ago for full price, $235k with multiple backup offers according to the agent.The property is 12 yrs old and feels like a worn rental.

I came across a property in the identical situation and am in the process of negotiating with the bank.

In Washington state we sometimes transfer in or out of an LLC and simply write "mere change of Identity" on the tax form.

If the tenant in this property were to cancel their lease, I would be able to cover the expenses myself from my salary.Being 28 and open to the ideas of taking more risk than someone more mature than myself, would you advise that I purchase a second property similar to the one I currently own, or go for a smaller property? 

I originally wrote if for Aussie investors.. but there is some good do's and don'ts in there from some one like me that has owned more than 400 of these.the industry as a whole has matured with the better TK operators really stepping up their game and the asset ... the main take aways are to remember that certain areas of the country and certainly the big rust belt cities and mid west cities have areas and neighborhoods you would never see in Idaho so you need to be very cognizant that RISK = REWARD in these markets. 

It matured earlier this month and it is still not renewed.

Not sure about the HELOC, I am currently in the same position as you with my first property being a duplex with almost identical numbers.

My broker created this pretty cool tool that identities properties that are undervalued in the market.

Having that many units would be very difficult to get any majority of them rented out via VRBO since you would likely have ~20 identical listings which wouldn't help sell your vacationers on staying with youINSTEAD: I rent out a studio apartment in my primary residence on AirBnB and have had enormous success.

I think this is EXTREMELY dangerous and I would say that it is a huge sign of maturity to seek critical feedback.