Never buy without personally inspecting and approving the property and INDEPENDENTLY, INDEPENDENTLY, INDEPENDENTLY, verifying everything from values to market rates, to approving tenant selection procedures and standards, to repairmen on standby, to everything else in Christendom that you can thing of.I am not a fan of out-of-state investing, especially for those with less than 50 years of experience, and for them, they’re probably too old for the hassle. 

Currently you have a STR lease and can effectively move anywhere the job market takes you.

Find some local meetups and start talking about your interests.

Years ago I bought houses for $25k in my market.

So many variables can turn a deal sideways from 1 hour to the next - i.e. inspection findings, title issues, contracts, financing issues, taxes, dept. of buildings/local municipalities, etc.I'm glad to hear you made it through the challenges, and it sounds like you'll be able to leverage this experience as you grow your portfolio.All the best to you along your journey!

As far as meetups go, you can find a lot of local events posted here on BiggerPockets: https://www.biggerpockets.com/forums/521-real-estate-events-...I also have a list of Chicago meetups that I can share with you as well.

If you want to network or ask specific questions about your local market, go to your local real estate forum and connect with investors from your area: https://www.biggerpockets.com/forums/86-local-real-estate-networking5.

Definitely recommend checking out local REI meetups in Boston now and Chicago later—tons of value in connecting with local investors.

I am considering getting into this space (looking at some courses), but worried that its too late, and that deep local market knowledge/understanding of buyers/connection with developers etc is required to make this work, which only incumbent/long term investors will have and would be hard for a new entrant starting from scratch to catch-up...is my hypothesis valid in your opinion ?

While I have none in this market I have been on one realtors monthly newsletter with market analysis for over 8 years.