What are your experiences with "boring" real estate?

Since I don't have the experience that I aspire to have yet, I'm looking to create a relationship with some guidance without being taken advantage of.

Good luck to you, it was a nightmare that I will never forget- great learning experience for me though!

Sounds like you’ve got some solid experience under your belt.

Their cost structures are significantly different from what new investors face today.Maybe I haven't yet reached the section that addresses different market conditions and interest rate environments, but I’d love to hear insights from those with more experience.

I run a MTR out of my primary bedroom and would be happy to connect and chat about your plans and what my experiences have been. 

2.Does anyone have experience investing in or house hacking in Danbury?

I’m giving serious consideration to converting into a PadSplit.However, I have heard that Fort Worth (the city, Tarrant County, the faceless boogey man…) has issues with PadSplit whereas Dallas County is supportive.I would love to hear about your experiences between the two markets and if Fort Worth can be viable for PadSplit and anything I should be mindful of?

I’m beginning to think that my experience differs from yours and others who have the same experience with sub to as you because almost all of my deals in the last 20 years have been COMMERCIAL properties; hence a significantly different species. 

STRs demand more time even though alot of things can be automated. you will managing cleaners, damage, guest experience, supplies, and more.4) Use AirDNA to see what an estimate of revenue can be, check Airbnb in your local neighborhood to see if anyone else if getting higher rates, and use BiggerPockets STR calculator to see what common expenses you may be forgetting.