Quote from @Jessica Miniru: Cold calling skills are great very few want to do it and that leaves it up to you to handle it and crush it for the people that do not want to do it.

The way to do this is through advertising here on BP and/OR attracting clients organically.Advertising will allow your company to be featured when someone clicks 'Build Your Investing Team' and Property Managers above.Attracting clients organically entails answering questions on these forums and sharing your expertise to help the community.BiggerPockets does not allow you to advertise on these forums (except the classified section) and that is a good thing.

Welcome to BP.

Welcome to BiggerPockets, Cody!

My biggest hesitation is that my closest profitable markets are about 3 hours away from where I live, so I’m figuring out whether that distance is going to make things harder than they need to be for a first deal.I’m here to learn, connect, and get advice from people who have been through this stage.If anyone has experience with:•managing a unit several hours away•starting with arbitrage vs. co-hosting•picking the right first marketI’d love to hear your perspective.Looking forward to being part of the community and learning from you all.Thanks! 

But at what point did you consider yourself at a "tipping point" or at a good spot to invest in a 2nd investment property and how did you go about doing so?

You should get some good tips and suggestions here.  

Quote from @Jimmy Lieu: Quote from @Zachary Rentz: Has anyone investigated with Rent to Retirement?

These are most time consuming, more capital intensive, and demanding to catch up to speed quickly to get to profitability. 

I run a small property management company in a small town, and I’m looking to refine our advertising strategy.