You get a deduction for the contribution, the gains grow tax-free and as long as you use the proceeds for health-related expenses the funds come out tax free as well. 

We even did a mid-year check in meeting in person but felt like he did not provide us any guidance.

This way, your current rental stays a cash-flowing asset while providing leverage to grow your portfolio.

Most landlords don’t go looking for a property manager until they’re dealing with an issue—tenant headaches, late rent, maintenance problems—so your marketing should focus on providing solutions, not just listing your services.Marketing Strategy: Combined or Separate?

Dallas-Fort Worth offers growth and opportunity, but smaller markets like Sioux Falls or Des Moines provide stability.

If I invested 100K today, they are currently providing anywhere from 60 to 72% passive tax deductions due to cost segregation, depreciation, etc. 

After several calls with some of the larger PMS providers, where I really took the time to dive into their products and compare features, pricing, and more, we've decided to go with Hostfully.

I’m looking for a local mentor that I can learn from and provide value to so any suggestions on how to find one and pitch myself would be great as well!

great advice provided - what I will add to this is if you have smokers and its not allowed I would offer to allow them out of the lease with no penalty. 

@Hector Lewis - The decision ultimately depends on your current cash reserves relative to your financial needs, as well as your willingness to reinvest for potential appreciation.