At our last turnover, we had neighborhood kids breaking in several times while vacant, damaging the house until we installed a security system and camera high enough that they’d need a ladder to get to it.

Part of being a landlord gives you the power to help people who need a break so it's in your hands to look at the record and say, that was a long time ago, now he has a good business.

Not advocating you break the law just letting you know what's going on in the marketplace. 

It sounds like you have the basic 20/25yr 3tab shingles, which yes are prone to "flip up" or break off, esp as they get older.Find another local Roofer, that for sure taunts that they do Repairs, will warranty their work, and get the repairs done. 

.- Lower down because I can do FHA loan- Probably don't need a property manager because I live here- With the potential rent income vs monthly mortgage price, I am probably breaking even if lucky- Pro tenantJacksonville:- Total cost of home is lower, even though I will have a higher down payment because I am buying it as an investment property- With the potential rent income vs monthly mortgage price, I might make a couple hundred a month... which can eventually be used as a down for another property?

The way you are breaking it down is very spreadsheet-friendly in terms of what would work in a best-case scenario, but landlording for five room hackers is not easy and the rent is not easy to collect in all cases.

Have not cash flowed the property for 2 years with her living there as she breaks everything (another reason she’s being served notice). 

Being at a slight operating profit or break even is completely fine with my though as I'm not looking at this as some get rich scheme, it's a long-term investment.Based on this, I'm looking now more into getting a more utilitarian STR targeted at business travelers where the goal is similar to my LTR's, getting long-term appreciation and mortgage pay down and making enough cash flow simply to cover repairs. 

One thing I wish I knew before my first deal was the importance of budgeting for long-term maintenance and unexpected expenses—it can make or break your cash flow.

We both have made compromises along the way.I think that’s completely right and one of the reasons you hear the horror stories about these things going sideways (there’s no established timeline for exit), it literally just goes until something breaks. figuring out the ownership structure, and thus the use/access, as well as the exit feels like the two biggest items to get extreme clarity around.