You'll want to have an insurance agent familiar with rentals since a lot of the extras on your coverage that you will want, the average insurance agent won't know to give you. 

It's like real estate agents, the bar is too low, but the brokerages like it that way because they make money off the agents who do no deals.

While it will likely give you more confidence and answer a lot of questions, I would say that talking to a seasoned investor, or even agent that works with investors, is a way better idea than spending 8K on something that you don't know too much about, especially before your first deal is done.

Real estate agents are not highly regulated in Costa Rica as opposed to North America.  

I am BP's Premiere Featured Agent for the WMass area.

I'd also recommend finding an investor-focused agent in that market, sharing with them your buy criteria, and then having them set you up with an email list for properties that get listed. 

Plus, if you'd like to connect and talk marketing/sales happy to do coffee or something.Also, there are tons of Facebook groups for Chicago real estate.Lastly, just doing some 1:1 networking with lenders, agents, and architects is something we focus heavily on.

If I am all in on the property for 360k (purchase and some finishing construction as well as carry costs) and the home is valued at 450k or more (based on what im told by agents as well as my own analysis while staying conservative), that is 20%+ equity I believe, unless I am missing something.

I will take on all the risk whilst always making sure the property is in a selling condition at all times and professionally cleaned and maintained, and if there's any damages my insurance would cover it.

Many investors use wholesalers or real estate agents who specialize in investment properties, or they directly target owners with distressed properties.5.