It is still repairable but would cost 800-1000 to repair, and probably has 3 years of life on it according to the inspector and roofers.3.

But they are also looking for clients for life IE they want all your banking all your CC if you use those things.. your retirements accounts etc etc..

You can usually get this for the project's life then switch back to renters/normal if needed.

I worry about you putting too much of your life into one investment given you're limitations on income/working situation anyway.In general expensive primary residences do not make the best rental properties. 

My goals would be to increase monthly cash flow and have more access to the property's equity for things like Cap Ex, etc....Here's a blurb from a lender's website:"By combining banking functionality with home financing into one dynamic instrument, borrowers are able to save tens of thousands of dollars and years off their loan""Designed after popular programs around the world, the All In One First Lien HELOC is the nation’s first transactional offset type-mortgage program.Home financing and banking combined:Deposits lower your loan’s principalFunds remain available for expensesInterest is calculated on the average daily balanceThis lowers the monthly interest paymentsTens of thousands of dollars can be saved over the life of the loanMortgage freedom can be achieved in half the time or less

look at other STR data in the area and do similar style to do your best to recreate similar results 

If the software is not simplifying your life or making you more accurate, you shouldn't use it.

And it's convenient for life if you use your personal bank account, you can still have one app for rentals and paying friends.-  Con's:  Nothing about the software per say, but about the landlord experience. 

The payback period is around 30 years, but the solar panels life is about 20 yrs.

A pro is sometimes you can apply your commission to your deals when buying as well as save a little when you're selling.A good instagram account to follow to give you an idea of the lifestyle of the vast majority of agents that are not investor friendly agents is @thebrokeagent - https://www.instagram.com/thebrokeagent/