@Emily Gowen so as you pointed out you would not have to do a 1031 exchange on your current home to avoid the capital gains tax and coupled with what Dave Foster pointed out I think, speaking from experience you would have a high likelihood of success. 

Many investors successfully build portfolios remotely, but thorough market research and assembling a strong local team (agent, lender, contractor, PM) are key.

I'd love to hear your feedback on success or struggles and anything I should expect.

I am looking for some feedback from others on their success/feedback on unique STR properties.

@Eric McClintockCongratulations on your success in the DMV area.

Quote from @Del Brady: Yes, many of us are introverts and successful in real estate investing.

The better your can run and manage that business the successful you will be.

Investment Info:

Single-family residence buy & hold investment in New Milford.

Purchase price: $140,000

Cash invested: $55,000

Sale price: $255,000

My business partner and I took on this Arli...

No offense, but hire a PMC because:1) You hate the process of placing tenants.2) You didn't do a very good job of screening the current ones.Sometimes we have to get out of our own way to find success!

Plenty of successful investors started right where you are.