Are you suggesting not to create an LLC at all and simply get umbrella insurance?

BP is an excellent source for vetting turnkey providers, simply by looking up the companies using the search function.

She then starts telling me how the previous owner was going to go half with her and all this jazz about cutting it down.....

This was pre internet days so immediate access to credit was not there Not the case I’m today’s world I guess the takeaway is always hire a good full time property manager upfront let them do what they get paid for and don’t cut corners Hiring a Realtor that is not a Property manager to find a tenant only and to save the monthly management fee Is Like going to the dentist and being told you need a route canal.

You're cash-flow negative so you take a giant cut with the $50K, 360 small $200/month cuts, and a big (or a ton more small) renovation cut.The big...big...BIG things you're missing are the net present value of money as well as the compounding profits. 

I think it would be better to simply actually open a savings account and put money in every month.

If they are simply a contractor and no partnership is in place - you would just pay them more in cash and report the amount on 1099-MISC.If they are a partner in a partnership - it gets a little bit tricky as normally allocation of income/expenses are dictated by the partnership agreement.

If you simply replaced a broken pane, that might be more of a repair than capex.

The electrical on that one is split.For us, and the option without knowing any more I'd recommend is to : We found the easiest thing to do was to pay the bills yourself and simply build what you think is the average utility bills attributable to each space into the rent price.In terms of marketing, market the place at the lower so you don't turn away people and then negotiate you paying those bills (the increase in rent functionallyThat said, there are other options but of course they involve cost. 

Simply because the house is off market and priced 50k below comps means nothing when it needs 50k in work it's still essentially market value.