- Is hurricane insurance covered in my condo fees or is this something I would have to pay out of pocket?

Depends on a lot of factors....sq. footage, does it involve the kitchen, bathrooms, etc. exterior changes, etc. $1000-3000+  That includes communication time, going out to the site to measure, etc.

@Andrew Stringfield how can you project if this will be a cashflowing rental without factoring into your calculations accurate taxes & insurance?

My friend did this and it ended up working out really nice and you basically have a new house but it’s a “renovation” and they didn’t have to put solar and pay certain fees etc.ADU is also very popular right now and seems easy to get the permits, but if it were me I would think long term about the property value if I intended to sell at some point. 

For those of you who actively choose to invest in high crime areas, what do you make sure to factor into your numbers?

To help you in your search: be sure to find an accountant who is willing to grow with you, and is not too high priced fee-wise.

There are folks who do turnkey differently (including us) where the headache of project management, finding tenants, and all of that stuff is taken care of without paying extra fees.

The set up cost for you to go with a broker would be no extra cost to you- the investor that borrows the money would pay the set up fee.

@Andrew Postell and @David M. ok gentlemen here is my takeaway from this is 1) I need to study tax code a lot and 2) the only way to mitigate his capital gains tax is probably going to look something like talking him into a master lease and paying him a monthly fee until the capital gains tax is paid for up to a previously agreed upon percent.

So, 26-32k profit and no 3% fee as closing costs on the selling side were factored in from the sound of it.