I dislike the thought of the property sitting vacant and costing me a few hundred dollars per month but I’d also hate for all off the money I just spent renovating the property to be a waste and I will have to redo everything over again.  

On a hundred units $30 is no big deal to a tenant but $36,000 a year is a pretty big deal to a landlord.

Small budgets of a few hundred dollars a month pushed towards Facebook or Google can help increase your brand awareness, start building audiences you can follow up with overtime and increase your lead count which will all increase your deal flow. 

There are probably hundreds if not thousands of posts in here on the topic. 

My guess is this might have to be in the hundred(s) of dollars to make it worth their time.

-Some will spend hundreds of hours training and testing you and others will just throw you in.

I was wondering, as time goes on (and hopefully) my portfolio grows, I’m wondering how to more experienced investors organize tens and/or hundreds of properties.

There are hundreds of different ways to start out.

The umbrella policy is a couple hundred bucks, and if you get sued, the insurance company is incentivized to hire a lawyer to protect you and keep them from having to pay out a large settlement.

That $10 / month notice could be worth hundreds of thousands of dollars.