It depends on your location as some areas / counties do not have this data available online,  You will likely get responses about real estate investor applications that can get you that information but cost a good chunk of cash and come with other features but you may not need.  

Your odds of something like this happening that will cost a fortune to remedy are a little more also. 

This will probably cost a total of $5,000 this month.You can make a lot with STR's, but they can be a lot of work and the income can be unreliable.

My brother and I are interested in potentially purchasing a small parcel of land and/or a property with a residence already in place where we could pursue an Air BnB/Vrbo strategy in Costa Rica. 

Earlier this year I purchased a property in the mountains of Costa Rica.

If you feel the property value is going to continue o rise and the house is not going to cost a lot to maintain over the next 10 years it may be best to keep it.

Yes hard work work is required either way but talking about a smoother process than say investing in Costa Rica or Germany?

Definitely get some estimates to see how much the roof repairs will cost, as well as redoing any interior stuff. 

May times they have a team of very good subs together who can build the project themselves, they cost a premium.

However if I did desire to evict someone I would try alternate methods first such as raising rents above market rent, cash for keys, etc. in part because an eviction can be a pain in San Diego (take a lot of time and cost a lot of money).I suspect the healthy economy and traditional low vacancy rates contribute to a lower need to evict tenants.