But painting the exterior of a house for $500 is very reasonable, at least around here for any person of reasonable skill to paint a house.  

I actually work in Huntsville on the base.

We are excited and eager to do things right, and we are willing to take reasonable risks.Some background: First I was a musician (two degrees), and now I'm an actuary (career switch when the pandemic started).

This can tell me a lot about the age of the plumbing, roof, HVAC, etc before actually walking it.

What you generally care about, however, is the actual & current revenue.Once you start to focus in on a property that looks like it might be a good fit, the next conversation is with a commercial mortgage broker (I would be one example, among many) to go over what the financing of that property might look like.

Here are some of the reasons for this: i had an insurance claim with my LLC about 5 years ago and now my insurance is through the roof, interest rates are slightly higher i use the LLC because I will be getting a mortgage.

Like, an actual PM? 

For that reason, I am planning to list it myself vs. using my broker and paying a fee.   

However, I talked to my realtor who got started in real estate via room rentals and he shared that as a 'border income' situation you actually have more rights than a traditional landlord.

If you are doing it for those reasons then you are going to have a rude awakening.