Hi John,I appreciate your perspective and experience!

In my experience one of my biggest lessons learned when dealing with older properties always expect more than you initially thought. 

The problem with Multi Family is that unless you or your partner have $10M or so of net worth and $1M in cash laying around as well as prior experience with commercial real estate, you can't get the loan. 

It’s a marathon not a 50 yard dash from my experience. 

You have tax benefits through depreciation and you are gaining experience via property management.  

Borrower experience: Will you lend to newbies?

Ask how many units they manage and how much experience they have.

If a home is titled in a trust (or an LLC), the trust or LLC should be added as an additional insured to avoid potential disputes during a claim.To confirm, we reached out to an insurance carrier, who clarified:“A carrier can potentially deny a claim if the home is titled in a trust or LLC but the insurance policy is under the individual homeowner's name.

In my experience, the best thing to do is warn people over and over again.

I'd check local STR FB groups and see if you have a local Real Estate Club.You can offer your services there, maybe for free in exchange for the experience.