Looking for lenders who you've seen are willing to issue a HELOC (or loan) in 2nd position on an investment property. 

I have an investment thats been stable. has not required much upkeeptwo years iv owned it without much difficulty finding renters hvac, roof without issues so far but are on the back end of expected life.  

I roughly had to pay a month’s rent for that maintenance issue.

Banks requires (2) months copies of your checking or account for the down payment.If you get the cash into the account 3 months prior it will "not" show as a large deposit that you have to source and show it came from a personal loan which then causes no issues in underwriting.

What else can i ask just to prevent potential issues with a tenant.  

Title companies have been reluctant to participate, however, we just closed a loan in Texas where the borrower signed remotely using a remote notarizatiion service and the title company accepted this and issue a title policy. 2.

@Amanda Scheller, @Eric Yu, that's what I was going to advise, link up with a real estate agent who focuses on house hack acquisition.

Common examples: Is there a maintenance charge with every call/issue? 

The biggest issue with using all cash is that it ties all your money up and denies you the leveraging power of using the banks money.  

Typically a HML will not lend on owner occupant property due to federal compliance issues.