I’d be happy to jump on a call with you or chat over a private message if you’re open to that.

I private messaged you. 

Of course I can switch carriers, but the question to you all, is are you noticing insurance carriers getting very picky with certain things, and if so, what?

The return on equity is probably very low considering they are paid off so maybe explore refinancing or selling the lowest performing one(s) or your biggest headaches to reinvest in more lucrative deals.I noticed you also used a metric of number of rentals to attain your goal rather than $$$/month.

While competition hadn't changed dramatically, we noticed some of the competition had pushed up rents on other 3 and 4 BRs in the area.  

When you buy a property with the intention to Airbnb Househack, you can find a better layout to make it more separate / private but start with what you have, Get temporarily uncomfortable so that you have a comfortable future.

We are considering becoming a private lender with them and I am doing some background research on him and his companies and wondering if anyone has done any deals with them.

I also noticed in the last hearing that they changed it to say 2 days in the last 2 years.  

You could form a month to month lease with a just a days notice to vacate so you could end it as soon as you get your license ready to close, the seller might be open to it.https://www.hostaway.com/blog/rental-arbitrage-joshua-tree/Or, you could continue to list on the seller's Airbnb and you could become a full-access co-host on their account - handle all communication, pricing, etc.

Quote from @Michael Smythe: Besides MANY self-labeled "gurus" exaggerating their success, many of them just supply readily available info.If you're too busy to find the info and are willing to pay for it, no problem as you accept their time vs money solution.REGARDING S8 GURU ISSUES SPECIFICALLYMost of them don't share all the facts about how Section 8 actually works.They claim you can get HIGHER rent from S8 tenants vs private-paying tenants.Why would the government allow our tax dollars to be spent this way?