In this market good tenants aren't difficult to find, so don't let the fear of vacancy stop you from getting rid of a problematic tenant. 

my biggest fear is not having enough reserve for a big unexpected item that comes up then I won't be able to pay back a loan or get the property fixed the way I want it to.

I think white would look much better, but I am worried that's going to be a lot more work and I also fear how well the white paint would hold up over time (they are rental units I know they'll take a beating and potentially chip/ scratch).

If you're investing blind then you have a multiple of disposable income or have no fear of loss.

This is the reason the best policy is to give regular/annual rent increase which would avoid your present landlord fears.Just send the notice in the email with the amount and date effective.You would be farther ahead if you did not fear the responsibilities of being a landlord and simply raise the rent to market or get a new tenant.

I also know that in many cases the llc will protect my personal assets and I fully believe this is either analysis paralysis or just fear of failure.Thoughts on how to get past this and where you recommend starting?

We do feel like we are throwing money away helping her with rent when we could be putting it towards an investment property instead, but there is always the fear of pulling the trigger on the first home that isn't your primary. 

Many of the investors I work with have a healthy fear of making a wrong or bad decision.

I’ll be honest, I am a bit fearful of him and how he could react.

@Gregory HerbertTruly market dependentSome sellers will List a home below market value with offers due by a date to spur excitement The whole fear of missing out which is absolutely true in the real world and in life.