If the deal is small enough and all investors can stay actively involved, you may be able to do a joint venture and keep your costs low.

I'll keep a closer eye and perhaps offer them a small decrease to incentivize them to stay if the price is out of line next spring.

I know this is asking a lot but is there a table or a guide that would show if you invest X your cashflow should be Y.

My question is do I need a more extensive of insurance policy with people staying on our property.  

Legally she can stay till the last minute.. 

It will stay there for another 50 years and not be a danger.If you have popcorn asbestos ceilings then paint them.

I think either would be fine, but would definitely stay away from Winter (October through February for sure).if you wanted to switch your leasing months you could do month to month for a while until March or April rolls around, then look for a year long lease!

They might stay.

Scotsman Guide has a great resources.. you can search which lenders lend in your states, and up to what %LTC / %ARV, their parameters, etc..

If you stay diligent and network with other investors, I'm sure you can turn that education and enthusiasm into success :)