I already invested in 2 properties the traditional way (conventional loans) but am realizing that money is always going to be an issue.

It was ok to go ahead to buy the property. 

You don't know at this point exactly what's going on, whether you just have an irritable tenant, or if the Lease is being violated.

And if so, what steps would you take first, and how would I go about reaching out to the landlords.

If this property is a lakefront cabin in Minnesota, my default advice would be to go the STR route. 

I’ve been thinking going the second home/ mid term/ str route. another thought I have is venture further into a rental property but I know with rates, finding a deal that would cash flow would be tough. 

San Antonio is going to be policing the permits and regularly sending a list to Airbnb and VRBO to delist.

Hi Casey,As the gentlemen's above mentioned, 20% out of $700K is indeed $140K, so the answers is yes.As a hard money lender, my 2 cents for you is that if you don't understand the loan structure in 100%, not 99% but 100%, don't go into it.BTW - As hard money lenders usually we charge less than 20%, but seems like this is a factor of maybe less experience you have.Anyhow good luck!

If the $45 rent increase + security is tough for the them, maybe you can go a little higher with the rent increase and not ask for the security.

FYI the interest of doing it in trusts would be to avoid probate and any inheritance taxes, but again, I'm just doing research and am not a lawyer so just trying to get more info so I know which direction to go and what to ask when I get things set up