In true Arbitrage, you also furnish and remodeled to make it viable for the short term rental market.I don't find myself agreeing with that assessment, because as the buyer said he made some mistakes.

@Dean Letfus thanks for quick and comprehensive reply.

Best way to do it is to use it is to search by zipcode then narrow it down with the filters to get an accurate assessment of what houses sold for in a particular location.

When you provide any kind of extra service to guests it changes the taxable nature of the rental.Julie, I am really looking forward to your assessment on this.

But first you have to look at yourself and assess what your appetite for risk and what you can actually spare money-wise to apply towards real estate investing.  

you may want to talk to a wealth manager one that charges a set fee.. and come up with a comprehensive plan that may or may not even include real estate.. real estate is work and risk.from all appearances you don't need to risk.  

The quarter acre lot is/was $75K assessed that sold for $80K.

What you need to do is call another PM company and get a rental assessment along with that you need to do some personal research yourself and see what neighboring homes are renting for. 

How do i properly assesss my personal finances to accurately determine the ceiling on the deals that i can afford?

Providing that the Reserve Study was competently produced and is current (should be current in California since that is the law), take a look at the 30-year funding plan paying close attention to the direction of the annual reserve contribution and whether there are any surprises such as future special assessments, bank loans, or large contribution jumps.