Maintenance fees are usually really high in HI and this one was reasonable at $650/mo with a pool, prime location, and 24hr security.

We are securing with loan at end... 

Because you likely won't be able to secure another FHA loan after your first purchase, starting with a bigger, more expensive property might be smarter, assuming that you don't have unlimited cash reserves.

Similarly, it's difficult to quantify how much a secure bike rack is worth, or the proximity to a bus stop.

What security system can be used so I can monitor activity there?  

Remember conventional all go through the same underwriting and end up on the same balance sheet (one of the governments secured entities) no mat who the originator is.

I would recommend talking to a securities attorney who specializes in real estate like Jillian Sidoti over at Crowd Funding Lawyers. 

@Susanita VanGood I see a lot of OKC investors using Aaron Chapman with Security National.

Once your loan is funded, it will be thrown into a mortgage backed security of 1000 mortgages (this is true even if the servicing does not change hands, mortgage servicing and mortgage ownership are divorced).

You might consider reaching out to Aaron Chapman at Security National to mark the lending aspect of things off your list!