I have no experience in real estate (in terms of buying any sort of property at all) and have found my way here for more information.

This sort of thing is not guaranteed.

Does the state of Florida have boilerplate agreements for this sort of arrangement, like they do for purchase agreements and rental agreements?

Is this typical?

Typically, if people don't want to list on MLS during a seller's market, it means either the property is not likely to qualify for traditional financing, which could work in your favor, or they want more than the property is actually worth and can't find an agent to agree on a listing price, which could be a major barrier- you might try to see if you can find this info out.

Hopefully it’s something innocuous like that - it’s sort of silly for him to pay for a dedicated internet connection or cell connection just for a camera or thermostat.

I typically spend up to 20% of my commissions on lead generation online and off.

I don't think you typically pay points on FHA, so that might be some upfront cash savings.Have you called other property managers to see what their opinions of the property and rents in the area are?

A lot of investors overlook the deals/opportunities that are already easily within grasp of their existing portfolio.Your analysis seems apt to me, obviously the 'your time' is hard to quantify - I'm not sure that the jump from 2 to 3 bedroom would enable getting less needy tenants - at least with what we're doing - I think this would actually typically be the reverse if I had to generalize. 

Typical rentals in Highland Park for a 2 BR 1 BA run about $800-$900.