I'm in the same boat, always on the lookout for more insights and cool connections.

However, with careful planning and preparation, obtaining financing is still possible.Keep in mind that setting up an LLC for your rental property won't directly impact your loan eligibility, but the experience you gain demonstrates valuable skills for commercial real estate investment.

Speaking with and networking with seasoned investors can yield insightful information, even if you are unable to actively participate in transactions.Seek for seasoned real estate investors for mentoring.

And that's because one loss on a bad deal can wipe out all my gains on many good deals.

This is a great insight, especially about whether they are the direct lender and the exit strategy.

if that is the case, do you believe that the saved cash flow after the renovation and normal expenses/emergency funds, etc. would be enough to gain a down payment on the next property within 1-2 years?

Usually, a seasoned, experienced real estate agent or broker could also provide insight to current market rules and the local sentiment regarding STRs that might influence future changes.Some markets have no restrictions. 

Any insights and or pointers to resources would be greatly appreciated!

Good to know this, thank you for your insight.  

If you lived in the property for 2/5 prior years you could sell without capital gains.