Anything down to the studs/foundation/roof/etc is a more in-depth reno.

Does the coa cover roof, lawn etc?

You can go high-end and spend $100K, or you can go mid range and still spend $100K because you needed to build a large deck on a steep slope with lumber costs at it's 2021 peak.

Any time there is a need for major maintenance, say a new AC unit or a new roof, the two cousins have to coordinate and get on the same page.

Thats if all the HVAC are in good conditions and roof. 

Do you know the difference between framing, siding, roofing, flooring, and wallboard nails as an example? 

I changed to a new provider this year, and got insurance at $1450, but had to replace a roof and water heater to do so. 

Unfortunately, I have quickly realized the mortgage is much too steep a payment to promote a net positive cashflow even with all rooms rented.

I just read a Bloomberg headline that insurance costs off the roof and SWFL real estate experiencing a downturn.

It'll take a few years but I think this area is going to show steep appreciation over the next 5 years and you can get a decent place that'll cash flow a little right now, more if rates drop and you refi and best of all, high appreciation over the next 5-10 years.