It may be a little too late since you accepted the insurance money already, but typically you would have a contractor in place (Ideally multiple quotes) before accepting the amount quoted to you by insurance.If your insurance company referred you this company though then after doing more research on them maybe they are the best option?

If you can find a deal that is assumable (you take over the seller's interest rate), that would be ideal.

The ideal situation is you inherit it after they pass tax free with the new higher basis.

Ideally, the tradesman identifies this and communicates it before they proceed.

Ideally I would like to keep my personal finances separate from my REI. 

Having young kids we’ve decided it’s best to not move around.Instead, my goal is to find an investment property in my local market (Rochester, NY), ideally a single family or duplex. 

Above is more my ideal scenario 

The proximity to hospitals , downtown fort myers & military presence makes it the ideal location. 

I know this is not ideal and I need to streamline into one PMS for future growth but am at a loss at what is available for different payout accounts to be associated with particular listings on OTAs. 

Low taxes, landlord friendly, job growth, and close proximity make it ideal for our of CA investors.