The ARV on this property is just under $100k and I am struggling to find lenders who are willing to lend on such a low dollar value.

If the tenant struggles to pay rent because they cannot budget and this is a problem then I would just upgrade the quality of the property you are renting. 

In this market, I'm really struggling with getting a new deal to pencil without a 25%+ downpayment.I have a new STR property that I expect to basically break-even on in terms of both cash and NOI over the next few years.

I'm struggling to find a nice way to reinforce the fact that I am not responsible for tenant's personal items.

I'm struggling to think of ways that I could generate valuable content for when the existing content goes stale...

It casts a dark shadow on an already struggling industry and opens the doors for more reform and regulation. 

We've managed to keep all of our accounting and bookkeeping in-house so I'd love to connect with more investors and to especially hear from those investors who are doing their own bookkeeping and accounting and any of your current struggles.

That process has been a struggle.

Even with that experience I, too, struggled to get started myself.

They do not want the discount broker they want one of the best in their field to put odds in their favor of buying a good investment.Since I am already wealthy I can tell them what I really think about a potential investment whereas the brokers needing that money in the moment to do a transaction struggle with paying their bills versus being completely open about what they think with an investment.