As I get more confident in my real estate knowledge I plan to actively learn by going to real estate meet-ups and meeting up with some local investors. 

Along with your confidence level that each of these cases might occur.Good Luck!

If not then you need to ask how confident are you in handling a real estate transaction yourself?

Congratulations on your success and have confidence you’ll keep overcoming obstacles and improving!

Seems like a pretty measured message sent in confidence. 

If you look up the deed that Amazon has in Ocala Florida, the property is literally $100 million and they were only issued a special warranty deed.A quitclaim deed, special warranty deed, and general warranty deed are fine in any deal ONLY IF the buyer is confident in their research or pays a title company or attorney. 

But I'd also like something a bit less intensive than a BRRRR to build confidence in my first deal, even if the cashflow is mediocre. 

As an old civil engineer I’m not confident that all those penetrations through shingles and membrane would stay water tight.  

Future investors might consider this and possibly look into local property management solutions if they're not able to frequently visit the site.Recommendations and Networking: Sharing contacts like Jeff Chisum who have proven helpful in your investment journey is beneficial for the community and helps foster reliable networks of professionals.Lessons Learned: Your insights into the challenges of managing a high-elevation STR during winter are invaluable.

I’ve watched multiple videos on the Biggerpockets channel and it's given me a bit more confidence.